Document:

Document

PROS Holdings, Inc.
NOTICE OF GRANT OF RESTRICTED STOCK UNITS
(U.S. Participants)

PROS Holdings, Inc., a Delaware corporation (the “Company”), pursuant to its 2017 Equity Incentive Plan (the “Plan”), hereby grants to the holder listed below (the “Participant”), an award (the “Award”) of Restricted Stock Units (the “Units”), each of which is a right to receive on the applicable Settlement Date one (1) share of Stock, on the terms and conditions set forth herein and in the Restricted Stock Units Award Agreement attached hereto (the “Award Agreement”) and the Plan, each of which are incorporated herein by reference. Unless otherwise defined herein, the terms defined in the Plan shall have the same defined meanings in this Grant Notice and the Award Agreement.  The Award is intended to provide for nonqualified deferred compensation that complies with all requirements of Section 409A of the Internal Revenue Code (“Section 409A”) necessary to avoid tax penalties under Section 409A.

												
		Participant:
	__________________

		Grant Date:
	__________________

		Number of Units:
	__________________ , subject to adjustment as provided by the Award Agreement

		Measurement Date:
	__________________

		Settlement Dates and Amounts:
	Except as provided by the Award Agreement, Units will be settled in accordance with Section 5 of the Award Agreement on the following dates and for the following percentages of the total Number of Units, provided that the Participant’s Service has not terminated before the applicable date:

			Settlement Date
	Settlement Percentage

			1st anniversary of Measurement Date
	25.00%
			5th quarter following Measurement Date
	6.25%
			6th quarter following Measurement Date
	6.25%
			7th quarter following Measurement Date
	6.25%
			8th quarter following Measurement Date
	6.25%
			9th quarter following Measurement Date
	6.25%
			10th quarter following Measurement Date
	6.25%
			11th quarter following Measurement Date
	6.25%
			12th quarter following Measurement Date
	6.25%
			13th quarter following Measurement Date
	6.25%
			14th quarter following Measurement Date
	6.25%
			15th quarter following Measurement Date
	6.25%
			16th quarter following Measurement Date
	6.25%

By their signatures below or by electronic acceptance or authentication in a form authorized by the Company, the Company and the Participant agree that the Award is governed by this Grant Notice and by the provisions of the Plan and the Award Agreement, both of which are incorporated herein by reference. The Participant acknowledges that copies of the Plan, the Award Agreement and the prospectus for the Plan are available on the Company’s internal web site and may be viewed and printed by the Participant for attachment to the Participant’s copy of this Grant Notice. The Participant represents that the Participant has read and is familiar with the provisions of the Plan and the Award Agreement, and hereby accepts the Award subject to all of its terms and conditions. The Participant accepts as binding, conclusive and final all decisions or interpretations of the Committee upon any questions arising under the Plan or relating to the Units.
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	PROS HOLDINGS, INC.
		PARTICIPANT

	By:
	__________________
		By:
	__________________

	

Name:
	

Stefan Schulz
		

Print Name:
	

__________________

	Title:
	Chief Financial Officer
			
	Address:
	3200 Kirby Drive
Suite 600
		
		Houston, TX 77098
		

ATTACHMENTS:     PROS Holdings, Inc. 2017 Equity Incentive Plan, as amended to the Grant Date; Restricted Stock Units Award Agreement. The prospectus for the Plan prepared in connection with the registration with the Securities and Exchange Commission (“SEC”) of the shares issuable pursuant to the Award is available on the SEC website at www.sec.gov.

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PROS Holdings, Inc.

RESTRICTED STOCK UNITS AWARD AGREEMENT
(U.S. Participants)

            PROS Holdings, Inc. (the “Company”) has granted to the Participant named in the Notice of Grant of Restricted Stock Units (the “Grant Notice”) to which this Restricted Stock Units Award Agreement (this “Award Agreement”) is attached an Award consisting of Restricted Stock Units (the “Units”) subject to the terms and conditions set forth in the Grant Notice and this Award Agreement.  The Award has been granted pursuant to the PROS Holdings, Inc. 2017 Equity Incentive Plan (the “Plan”), as amended to the Grant Date, the provisions of which are incorporated herein by reference.

1.Definitions and Construction.

1.1    Definitions.  Unless otherwise defined herein, capitalized terms shall have the meanings assigned to such terms in the Grant Notice or the Plan.

(a)    “Change in Control” means a Change in Control as defined by the Plan, provided that the event constituting the Change in Control also constitutes a change in ownership or effective control of the Company or a change in the ownership of a substantial portion of the assets of the Company within the meaning of the Section 409A Regulations.

(b)    “Disabled” means, unless otherwise permitted by the Section 409A Regulations, that the Participant has been determined by the Company to be either:

(i)    unable to engage in any substantial gainful activity by reason of any medically determinable physical or mental impairment that can be expected to result in death or can be expected to last for a continuous period of not less than 12 months; or

(ii)    by reason of any medically determinable physical or mental impairment that can be expected to result in death or can be expected to last for a continuous period of not less than 12 months, receiving income replacement benefits for a period of not less than three months under an accident and health plan covering employees of the Participant’s employer.

(c)    “Dividend Equivalent Units” mean additional Restricted Stock Units credited pursuant to Section 3.3.

(d)    “Qualifying Termination” means the Participant’s Separation from Service within eighteen (18) months after a Change in Control, which separation results from either (i) the Participating Company Group’s involuntary termination of the Participant’s Service without Cause or (ii) the Participant’s voluntary termination of Service after a reduction of the Participant’s base salary by fifteen percent (15%) or more without the Participant’s express written consent, provided that the Participant has provided written notice to the Company of such reduction in base salary within sixty (60) days following such reduction and the Company has failed to cure such reduction within thirty (30) days following the date of such written notice.

(e)    “Retirement” means that the Participant’s Service is voluntarily terminated by the Participant upon satisfaction of all of the following conditions as of the date of the Participant’s Separation from Service:
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(i)    the Participant has been in continuous Service with the Participating Company Group for a period of not less than five (5) years;

(ii)    the Participant has accumulated a combination of at least sixty-five (65) retirement points, determined by the sum of the Participant’s attained age in years and the number of full years of the Participant’s continuous Service with the Participating Company Group;

(iii)    the Participant provided the Company with at least twelve (12) months’ advance written notice of the Participant’s intention to retire;

(iv)    the Participant has been determined by the Company, in its reasonable discretion, to have successfully participated in the succession and transition of the Participant’s duties with the Participating Company Group; and

(v)    the Participant has executed and allowed to become irrevocable on or before the sixtieth (60th) day following the date of Retirement a general release of claims against the Participating Company Group, its officers, directors, employees and affiliates in a form provided by the Company.

(f)    “Section 409A Regulations” mean the Treasury Regulations issued pursuant to Section 409A.

(g)    “Separation from Service” means the Participant’s separation from service within the meaning of the Section 409A Regulations.

(h)    “Units” mean the Restricted Stock Units originally granted pursuant to the Award and the Dividend Equivalent Units credited pursuant to the Award, as both shall be adjusted from time to time pursuant to Section 8.

1.2    Construction.  Captions and titles contained herein are for convenience only and shall not affect the meaning or interpretation of any provision of this Award Agreement. Except when otherwise indicated by the context, the singular shall include the plural and the plural shall include the singular.  Use of the term “or” is not intended to be exclusive, unless the context clearly requires otherwise.

2.    Administration.

The Committee shall have the power to interpret the Plan, the Grant Notice and this Award Agreement and to adopt such rules for the administration, interpretation and application of the Plan as are consistent therewith and to interpret, amend or revoke any such rules. All actions taken and all interpretations and determinations made by the Committee in good faith shall be final and binding upon the Participant, the Company and all other interested persons. No member of the Committee or the Board shall be personally liable for any action, determination or interpretation made in good faith with respect to the Plan, the Grant Notice, this Award Agreement or the Units.

3.    The Award.

3.1    Grant of Units.  On the Grant Date, the Participant shall acquire, subject to the provisions of this Award Agreement, the total Number of Units set forth in the Grant Notice, subject to adjustment as provided in Section 3.3 and Section 8.  Each Unit represents a right to receive on a date determined in accordance with the Grant Notice and this Award Agreement one (1) share of Stock.

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3.2    No Monetary Payment Required.  The Participant is not required to make any monetary payment (other than applicable tax withholding, if any) as a condition to receiving the Units or shares of Stock issued upon settlement of the Units, the consideration for which shall be past services actually rendered or future services to be rendered to a Participating Company or for its benefit.  Notwithstanding the foregoing, if required by applicable law, the Participant shall furnish consideration in the form of cash or past services rendered to a Participating Company or for its benefit having a value not less than the par value of the shares of Stock issued upon settlement of the Units.

3.3    Dividend Equivalent Units.  On the date that the Company pays a cash dividend to holders of Stock generally, the Participant shall be credited with a number of additional whole Dividend Equivalent Units determined by dividing (a) the product of (i) the dollar amount of the cash dividend paid per share of Stock on such date and (ii) the sum of the total Number of Units and the number of Dividend Equivalent Units previously credited to the Participant pursuant to the Award and which have not been settled or forfeited pursuant to the Company Reacquisition Right (as defined below) as of such date, by (b) the Fair Market Value per share of Stock on such date.  Any resulting fractional Dividend Equivalent Unit shall be rounded to the nearest whole number.  Such additional Dividend Equivalent Units shall be subject to the same terms and conditions and shall be settled or forfeited in the same manner and at the same time as the Restricted Stock Units originally subject to the Award with respect to which they have been credited.

4.    Company Reacquisition Right.

4.1    Grant of Company Reacquisition Right. In the event that the Participant’s Service terminates for any reason other than due to death, having become Disabled, Qualifying Termination or Retirement, all as set forth below, the Participant shall immediately forfeit and the Company shall automatically reacquire all Units for which the Settlement Date has not yet occurred as of the time of such termination, and the Participant shall not be entitled to any payment therefor (such forfeiture being referred to as the “Company Reacquisition Right”).

(a)    Death or Disability.  In the event that the Participant dies or becomes Disabled (without regard to whether or not the Participant has experienced a Separation from Service), none of the Units that have not previously been settled shall be subject to the Company Reacquisition Right and instead shall be settled in full in accordance with Section 5 within sixty (60) days following the date of such death or disability on a date determined solely by the Company.

(b)    Qualifying Termination.  In the event of the Participant’s Qualifying Termination and provided that the Participant has executed and allowed to become irrevocable on or before the sixtieth (60th) day following the date of such separation a general release of claims against the Participating Company Group, its officers, directors, employees and affiliates in a form provided by the Company, none of the Units that have not previously been settled shall be subject to the Company Reacquisition Right and instead shall be settled in full in accordance with Section 5 on the sixtieth (60th) day following the date of Qualifying Termination.

(c)    Retirement.  In the event of the Participant’s Retirement, none of the Units that have not previously been settled and that have Settlement Dates scheduled, in accordance with the Grant Notice, to occur within twenty-four (24) months following the date of the Participant’s Retirement (the “Post-Retirement Period”), if any, shall be subject to the Company Reacquisition Right, and such Units shall instead be settled on their respective Settlement Date(s) in accordance with Section 5 (but no sooner than the sixtieth (60th) day following the Retirement date); provided, however, that if the Participant breaches any of the Post-Retirement Covenants set forth in Section 4.2, then the Participant shall forfeit and the Company shall automatically reacquire all Units for which the Settlement Date has not yet occurred as of the time of such breach.  All Units having Settlement Dates scheduled in accordance with the Grant Notice later than completion of the Post-Retirement Period shall be immediately forfeited pursuant to the Company Reacquisition Right and the Participant shall not be entitled to any payment therefor.
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4.2    Post-Retirement Covenants.  The Participant acknowledges that the confidential information, special training, and/or other knowledge the Participant has and will receive through the Participant’s Service and at the Company’s expense relates to the Company’s business interests and would benefit both the Company’s competitors and the Company after the Participant’s Retirement.  The Participant recognizes a just purpose in the Company protecting such investments and interests, including through avoiding, for a limited time, competition by former employees trained with and/or given special knowledge, contacts, and/or experience by the Company.  During the period ending on the earlier of (a) the last Settlement Date occurring during the Post-Retirement Period or (b) the date occurring twenty-four (24) months following the date of the Participant’s Retirement, and in consideration of receiving Confidential Information and specialized training and knowledge, the Participant shall not (i) directly or indirectly engage in employment, including self-employment, that involves the Participating Company Group’s product lines, services and business interests during or as of the end of the Participant’s Service with the Participating Company Group, or (ii) solicit or encourage any customer or prospect of the Participating Company, with whom the Participant had contact during the twelve (12) months preceding the termination of the Participant’s Service, to terminate or diminish its relationship with the Participating Company Group (together, the “Post-Retirement Covenants”).  The Participant acknowledges and agrees that the foregoing restrictions are no broader than necessary to protect the Participating Company Group’s goodwill and/or legitimate business interests.  In the event a court of competent jurisdiction determines that the geographic area, duration, or scope of activity of any restriction under this Section 4.2 is unenforceable, the restrictions under this Section will be modified to the extent required to render them valid and enforceable.

4.3    Ownership Change Event, Non-Cash Dividends, Distributions and Adjustments.  Upon the occurrence of an Ownership Change Event, a dividend or distribution to the stockholders of the Company paid in shares of Stock or other property, or any other adjustment upon a change in the capital structure of the Company as described in Section 8, any and all new, substituted or additional securities or other property (other than regular, periodic cash dividends paid on Stock pursuant to the Company’s dividend policy, which shall be treated in accordance with Section 3.3) to which the Participant is entitled by reason of the Participant’s ownership of Units shall be immediately subject to the Company Reacquisition Right and included in the terms “Units” for all purposes of the Company Reacquisition Right with the same force and effect as the Units immediately prior to the Ownership Change Event, dividend, distribution or adjustment, as the case may be.

5.    Settlement of the Award.

5.1    Issuance of Shares of Stock.  Subject to the provisions of Section 5.3, the Company shall issue to the Participant on the Settlement Date with respect to each Unit to be settled on such date one (1) share of Stock.  The Settlement Date with respect to a Unit shall be the date applicable to such Unit as provided by the Grant Notice; provided, that if the Settlement Date falls on a day the principal securities exchange on which the Stock is listed for trading is closed, then the Settlement Date shall be the next day on which the applicable securities exchange is open for trading.  Shares of Stock issued in settlement of Units shall not be subject to any restriction on transfer other than any such restriction as may be required pursuant to Section 5.3, Section 6 or the Company’s Insider Trading Policy.

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5.2    Beneficial Ownership of Shares; Certificate Registration.  The Participant hereby authorizes the Company, in its sole discretion, to deposit any or all shares acquired by the Participant pursuant to the settlement of the Award with the Company’s transfer agent, including any successor transfer agent, to be held in book entry form, or to deposit such shares for the benefit of the Participant with any broker with which the Participant has an account relationship of which the Company has notice.  Except as provided by the foregoing, a certificate for the shares acquired by the Participant shall be registered in the name of the Participant, or, if applicable, in the names of the heirs of the Participant.

5.3    Restrictions on Grant of the Award and Issuance of Shares.  The grant of the Award and issuance of shares of Stock upon settlement of the Award shall be subject to compliance with all applicable requirements of federal, state or foreign law with respect to such securities.  No shares of Stock may be issued hereunder if the issuance of such shares would constitute a violation of any applicable federal, state or foreign securities laws or other law or regulations or the requirements of any stock exchange or market system upon which the Stock may then be listed.  The inability of the Company to obtain from any regulatory body having jurisdiction the authority, if any, deemed by the Company’s legal counsel to be necessary to the lawful issuance of any shares subject to the Award shall relieve the Company of any liability in respect of the failure to issue such shares as to which such requisite authority shall not have been obtained.  As a condition to the settlement of the Award, the Company may require the Participant to satisfy any qualifications that may be necessary or appropriate, to evidence compliance with any applicable law or regulation and to make any representation or warranty with respect thereto as may be requested by the Company.

5.4    Fractional Shares.  The Company shall not be required to issue fractional shares upon the settlement of the Award.

6.    Tax Withholding.

6.1    In General.  At the time the Grant Notice is executed, or at any time thereafter as requested by a Participating Company, the Participant hereby authorizes withholding from payroll and any other amounts payable to the Participant, and otherwise agrees to make adequate provision for, any sums required to satisfy the federal, state, local and foreign tax (including any social insurance) withholding obligations of the Participating Company (the “Tax Withholding Obligation”), if any, which arise in connection with the Award, the vesting of Units or the issuance of shares of Stock in settlement thereof.  The Company shall have no obligation to deliver shares of Stock until the Tax Withholding Obligation has been satisfied by the Participant.

6.2    Assignment of Sale Proceeds.  The Participant’s acceptance of this Award constitutes the Participant’s instruction and authorization to the Company and any brokerage firm determined acceptable to the Company for such purpose to sell on the Participant’s behalf a whole number of shares of Stock from those shares of Stock issuable to the Participant as the Company determines to be appropriate to generate cash proceeds sufficient to satisfy the Tax Withholding Obligation.  Such shares of Stock will be sold on the trading day immediately following the Tax Withholding Obligation arising (e.g., a Settlement Date or other date on which the Units cease to be subject to the Company Reacquisition Right) or as soon thereafter as practicable. The Participant acknowledges that the Company or its designee is under no obligation to arrange for such sale at any particular price, and that the proceeds of any such sale may not be sufficient to satisfy the Tax Withholding Obligation.  Accordingly, the Participant agrees to pay to the Company or any of its subsidiaries as soon as practicable, including through additional payroll withholding, any amount of the Tax Withholding Obligation that is not satisfied by the sale of shares of Stock described above.  The Participant agrees to indemnify and hold the Company harmless from any losses or damages relating to any such sale.

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6.3    Withholding in Shares.  The Company shall have the right, but not the obligation, to require the Participant to satisfy all or any portion of the Tax Withholding Obligation by deducting from the shares of Stock otherwise deliverable to the Participant in settlement of the Award a number of whole shares having a fair market value, as determined by the Company as of the date on which the Tax Withholding Obligation arise, not in excess of the amount of such Tax Withholding Obligation determined by the applicable minimum statutory withholding rates if required to avoid liability classification of the Award under generally accepted accounting principles in the United States.

7.    Effect of Change in Control.

7.1    If Award is Assumed, Continued or Substituted For.  In the event of a Change in Control, the Award shall be subject to the definitive agreement entered into by the Company in connection with the Change in Control.  The surviving, continuing, successor, or purchasing entity or parent thereof, as the case may be (the “Acquiror”), may, without the consent of the Participant, assume or continue in full force and effect the Company’s rights and obligations under all or any portion of the outstanding Units or substitute for all or any portion of the outstanding Units substantially equivalent rights with respect to the Acquiror’s stock.  For purposes of this Section, a Unit shall be deemed assumed if, following the Change in Control, the Unit confers the right to receive, subject to the terms and conditions of the Plan and this Award Agreement, the consideration (whether stock, cash, other securities or property or a combination thereof) to which a holder of a share of Stock on the effective date of the Change in Control was entitled (and if holders were offered a choice of consideration, the type of consideration chosen by the holders of a majority of the outstanding shares of Stock); provided, however, that if such consideration is not solely common stock of the Acquiror, the Committee may, with the consent of the Acquiror, provide for the consideration to be received upon settlement of the Unit to consist solely of common stock of the Acquiror equal in Fair Market Value to the per share consideration received by holders of Stock pursuant to the Change in Control.

7.2    If Award is not Assumed, Continued or Substituted For.  If the Award is neither assumed or continued by the Acquiror in connection with the Change in Control nor replaced by substantially equivalent rights with respect to the Acquiror’s stock pursuant to a substituted Acquiror award, then, pursuant to Section 15.4(f) of the Plan, the Award shall be converted automatically and without the consent of the Participant into a right to receive in cash on the applicable Settlement Date(s) in accordance with the Grant Notice occurring after the date of the Change in Control with respect to each Unit to be settled on such date an amount equal to the Fair Market Value as of the time of the Change in Control of the consideration (whether stock, cash, other securities or property or a combination thereof) to which a holder of a share of Stock on the effective date of the Change in Control was entitled (and if holders were offered a choice of consideration, the type of consideration chosen by the holders of a majority of the outstanding shares of Stock).

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8.    Adjustments for Changes in Capital Structure.

Subject to any required action by the stockholders of the Company and the requirements of Section 409A to the extent applicable, in the event of any change in the Stock effected without receipt of consideration by the Company, whether through merger, consolidation, reorganization, reincorporation, recapitalization, reclassification, stock dividend, stock split, reverse stock split, split-up, split-off, spin-off, combination of shares, exchange of shares, or similar change in the capital structure of the Company, or in the event of payment of a dividend or distribution to the stockholders of the Company in a form other than Stock (other than regular, periodic cash dividends paid on Stock pursuant to the Company’s dividend policy) that has a material effect on the Fair Market Value of shares of Stock, appropriate and proportionate adjustments shall be made in the number of Units subject to the Award and/or the number and kind of shares or other property to be issued in settlement of the Award, in order to prevent dilution or enlargement of the Participant’s rights under the Award.  For purposes of the foregoing, conversion of any convertible securities of the Company shall not be treated as “effected without receipt of consideration by the Company.”  Any and all new, substituted or additional securities or other property (other than regular, periodic cash dividends paid on Stock pursuant to the Company’s dividend policy, which shall be treated in accordance with Section 3.3) to which the Participant is entitled by reason of ownership of Units acquired pursuant to this Award will be immediately subject to the provisions of this Award on the same basis as all Units originally acquired hereunder.  Any fractional Unit or share resulting from an adjustment pursuant to this Section shall be rounded down to the nearest whole number.  Such adjustments shall be determined by the Committee, and its determination shall be final, binding and conclusive.

9.    Rights as a Stockholder, Director, Employee or Consultant.

The Participant shall have no rights as a stockholder with respect to any shares which may be issued in settlement of this Award until the date of the issuance of such shares (as evidenced by the appropriate entry on the books of the Company or of a duly authorized transfer agent of the Company).  No adjustment shall be made for dividends, distributions or other rights for which the record date is prior to the date the shares are issued, except as provided in Section 3.3 and Section 8.  If the Participant is an Employee, the Participant understands and acknowledges that, except as otherwise provided in a separate, written employment agreement between a Participating Company and the Participant, the Participant’s employment is “at will” and is for no specified term.  Nothing in this Award Agreement shall confer upon the Participant any right to continue in the Service of a Participating Company or interfere in any way with any right of the Participating Company Group to terminate the Participant’s Service at any time.

10.    Legends.

The Company may at any time place legends referencing any applicable federal, state or foreign securities law restrictions on all certificates representing shares of stock issued pursuant to this Award Agreement.  The Participant shall, at the request of the Company, promptly present to the Company any and all certificates representing shares acquired pursuant to this Award in the possession of the Participant in order to carry out the provisions of this Section.

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11.    Compliance with Section 409A.

This Award is intended to provide for nonqualified deferred compensation that complies with all requirements of Section 409A.  It is intended that any election, payment or benefit which is made or provided pursuant to or in connection with this Award shall comply in all respects with the applicable requirements of Section 409A (including applicable regulations or other administrative guidance thereunder, as determined by the Committee in good faith) to avoid the unfavorable tax consequences provided therein for non‐compliance. In connection with effecting such compliance with Section 409A, the following shall apply:

11.1    Separation from Service; Required Delay in Payment to Specified Employee.  Notwithstanding anything set forth herein to the contrary, no amount payable pursuant to this Award Agreement on account of the Participant’s termination of Service which constitutes a “deferral of compensation” within the meaning of the Section 409A Regulations shall be paid unless and until the Participant has incurred a Separation from Service.  Furthermore, to the extent that the Participant is a “specified employee” within the meaning of the Section 409A Regulations as of the date of the Participant’s Separation from Service, no amount that constitutes a deferral of compensation which is payable on account of the Participant’s Separation from Service shall be paid to the Participant before the date (the “Delayed Payment Date”) which is first day of the seventh month after the date of the Participant’s Separation from Service or, if earlier, the date of the Participant’s death following such Separation from Service.  All such amounts that would, but for this Section, become payable prior to the Delayed Payment Date will be accumulated and paid on the Delayed Payment Date.

11.2    Other Changes in Time of Payment.  Neither the Participant nor the Company shall take any action to accelerate or delay the payment of any benefits under this Award Agreement in any manner which would not be in compliance with the Section 409A Regulations.

11.3    Amendments to Comply with Section 409A; Indemnification.  Notwithstanding any other provision of this Award Agreement to the contrary, the Company is authorized to amend this Award Agreement, to void or amend any election made by the Participant under this Award Agreement and/or to delay the payment of any monies and/or provision of any benefits in such manner as may be determined by the Company, in its discretion, to be necessary or appropriate to comply with the Section 409A Regulations without prior notice to or consent of the Participant. The Participant hereby releases and holds harmless the Company, its directors, officers and stockholders from any and all claims that may arise from or relate to any tax liability, penalties, interest, costs, fees or other liability incurred by the Participant in connection with the Award, including as a result of the application of Section 409A.

11.4    Advice of Independent Tax Advisor.  The Company has not obtained a tax ruling or other confirmation from the Internal Revenue Service with regard to the application of Section 409A to the Award, and the Company does not represent or warrant that this Award Agreement will avoid adverse tax consequences to the Participant, including as a result of the application of Section 409A to the Award.  The Participant hereby acknowledges that he or she has been advised to seek the advice of his or her own independent tax advisor prior to entering into this Award Agreement and is not relying upon any representations of the Company or any of its agents as to the effect of or the advisability of entering into this Award Agreement.

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12.    Miscellaneous Provisions.

12.1    Amendment. The Committee may amend this Award Agreement at any time; provided, however, that except as provided in Section 7 in connection with a Change in Control, no such amendment may have a materially adverse effect on the Participant’s rights under this Award Agreement without the consent of the Participant except to the extent such amendment is necessary to comply with applicable law. No amendment to this Award Agreement shall be effective unless in writing.

12.2    Nontransferability of the Award. Prior to the issuance of shares of Stock on the applicable Settlement Date, neither this Award nor any Vested Units subject to this Award shall be subject in any manner to anticipation, alienation, sale, exchange, transfer, assignment, pledge, encumbrance, or garnishment by creditors of the Participant or the Participant’s beneficiary, except transfer by will or by the laws of descent and distribution.  All rights with respect to the Award shall be exercisable during the Participant’s lifetime only by the Participant or the Participant’s guardian or legal representative.

12.3    Further Instruments.  The parties hereto agree to execute such further instruments and to take such further action as may reasonably be necessary to carry out the intent of this Award Agreement.

12.4    Binding Effect.  This Award Agreement shall inure to the benefit of the successors and assigns of the Company and, subject to the restrictions on transfer set forth herein, be binding upon the Participant and the Participant’s heirs, executors, administrators, successors and assigns.

12.5    Notices.  Any notice required to be given or delivered to the Company shall be in writing and addressed to the Company at its principal corporate offices. Any notice required to be given or delivered to the Participant shall be in writing and addressed to the Participant at the address maintained for the Participant in the Company’s records or at the address of the local office of the Company or of any other Participating Company at which the Participant works. A notice shall be deemed effectively given upon deposit in the U.S. Post Office or foreign postal service, by registered or certified mail, or with a nationally recognized overnight courier service, with postage and fees prepaid.

12.6    Electronic Delivery and Signature.  

(a)    The Plan documents, which may include but do not necessarily include: the Plan, the Grant Notice, this Award Agreement, the Plan Prospectus, and any reports of the Company provided generally to the Company’s stockholders, may be delivered to the Participant electronically. In addition, if permitted by the Company, the Participant may deliver electronically the Grant Notice to the Company or to such third party involved in administering the Plan as the Company may designate from time to time. Such means of electronic delivery may include but do not necessarily include the delivery of a link to a Company intranet or the Internet site of a third party involved in administering the Plan, delivery via e-mail or such other means of electronic delivery specified by the Company. Any and all such documents may be electronically signed.

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(b)    The Participant acknowledges that the Participant has read Section 12.6(a) and consents to the electronic delivery of the Plan documents and, if permitted by the Company, the delivery of the Grant Notice, as described in Section 12.6(a). The Participant acknowledges that he or she may receive from the Company a paper copy of any documents delivered electronically at no cost to the Participant by contacting the Company by telephone or in writing. The Participant further acknowledges that the Participant will be provided with a paper copy of any documents if the attempted electronic delivery of such documents fails. Similarly, the Participant understands that the Participant must provide the Company or any designated third party administrator with a paper copy of any documents if the attempted electronic delivery of such documents fails.  The Participant may revoke his or her consent to the electronic delivery of documents described in Section  12.6(a) or may change the electronic mail address to which such documents are to be delivered (if Participant has provided an electronic mail address) at any time by notifying the Company of such revoked consent or revised e-mail address by telephone, postal service or electronic mail.  The Participant understands that he or she is not required to consent to electronic delivery of documents described in Section 12.6(a). Finally, the Participant agrees that any and all Plan documents requiring a signature may be electronically signed and that such electronic signature shall have the same effect as handwritten signature for the purposes of validity, enforceability and admissibility.

12.7    Integrated Agreement.  The Grant Notice, this Award Agreement and the Units evidenced hereby (i) are made and granted pursuant to the Plan and are in all respects limited by and subject to the terms of the Plan, and (ii) constitute the entire agreement between the Participant and the Company on the subject matter hereof and supersede all proposals, written or oral, and all other communications between the parties related to the subject matter. To the extent contemplated herein or therein, the provisions of the Grant Notice, this Award Agreement and the Plan shall survive any settlement of the Award and shall remain in full force and effect.

12.8    Governing Law.  The interpretation, performance and enforcement of this Award Agreement shall be governed by the laws of the State of Texas, U.S.A. without regard to the conflict-of-laws rules thereof or of any other jurisdiction.

12.9    Counterparts.  The Grant Notice may be executed in counterparts, each of which shall be deemed an original, but all of which together shall constitute one and the same instrument.

12.10    Severability.  If any provision of this Award Agreement is held to be unenforceable for any reason, it shall be adjusted rather than voided, if possible, in order to achieve the intent of the parties to the extent possible.  In any event, all other provisions of this Award Agreement shall be deemed valid and enforceable to the full extent possible.

12.11    Relocation Outside the United States.  If the Participant relocates to a country outside the United States, the Company reserves the right to impose other requirements on the Participant’s participation in the Plan, on the Units and on any shares acquired under the Plan, to the extent the Company determines necessary or advisable in order to comply with local law or facilitate the administration of the Plan, and to require the Participant to sign any additional agreements or undertakings that may be necessary to accomplish the foregoing.

[remainder of page intentionally left blank]

12Exhibit 4.1

 

THIS NOTE, AND THE SECURITIES ISSUABLE UPON CONVERSION
OF THIS NOTE, HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE APPLICABLE
SECURITIES LAWS OF ANY STATE, AND MAY NOT BE PLEDGED, SOLD, ASSIGNED OR OTHERWISE TRANSFERRED EXCEPT AS PERMITTED UNDER THE ACT
AND APPLICABLE STATE SECURITIES LAWS, PURSUANT TO REGISTRATION UNDER SUCH LAWS OR AN EXEMPTION FROM SUCH REGISTRATION REQUIREMENT. INVESTORS
SHOULD BE AWARE THAT THEY MAY BE REQUIRED TO BEAR THE FINANCIAL RISKS OF THIS INVESTMENT FOR AN INDEFINITE PERIOD OF TIME. THE ISSUER
OF THESE SECURITIES MAY REQUIRE AN OPINION OF COUNSEL, IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER, TO THE EFFECT
THAT SUCH PLEDGE, SALE, ASSIGNMENT OR TRANSFER IS EXEMPT FROM THE REGISTRATION REQUIREMENTS OF THE ACT AND ALL APPLICABLE STATE SECURITIES
LAWS. 

 

ENTASIS THERAPEUTICS HOLDINGS INC.

 

Convertible Promissory Note

 

	$15,000,000.00	February 18,
    2022

 

For value received, Entasis
Therapeutics Holdings Inc., a Delaware corporation (the “Company”), hereby promises to pay to the order of Innoviva
Strategic Opportunities LLC (hereinafter referred to, together with its successors in title and assigns, as the “Holder”),
the principal sum of Fifteen Million Dollars ($15,000,000.00), together with any unpaid interest thereon as set forth below, unless earlier
converted or cancelled pursuant to the terms and conditions set forth below. The outstanding principal of this Note, together with any
unpaid interest thereon, is hereinafter referred to as the “Amount Due.”

 

This Convertible Promissory
Note (this “Note”) is issued by the Company pursuant to that certain Securities Purchase Agreement, dated as of February 17,
2022, by and between the Company and the Holder (the “Purchase Agreement”). Capitalized terms used but not otherwise
defined herein shall have the meanings ascribed to them in the Purchase Agreement.

 

1.            Maturity
and Interest. This Note shall mature and shall become payable on August 18, 2022 (the “Maturity Date”) unless
earlier converted or cancelled pursuant to the terms set forth herein. This Note shall bear interest from, and including, the date of
issuance at a rate of 0.59% per annum to, but excluding, the date of repayment or conversion of the Note. Interest on the Note shall
be computed on the basis of the actual number of days elapsed and a year of 360 days and shall be payable at the Maturity Date. From
and including the Maturity Date, if not converted, and for such time that this Note remains outstanding, this Note shall bear default
interest at a rate of 10.00% per annum (the “Default Rate”), which shall accrue daily and compound monthly to, but
excluding, the date of repayment or conversion of the Note. To the extent that any rate of interest set forth in this Note is higher
than the maximum percentage permitted by law, or lower than the lowest percentage permitted by law to allow this Note to be classified
as indebtedness for United States federal tax purposes, such rate shall be automatically adjusted to such highest or lowest rate (as
applicable) permitted by law.

 

    

     

    

 

2.            Amount
Due.

 

2.1            Payments.
Payment of the Amount Due shall be made in immediately available funds in lawful currency of the United States of America at the offices
of the Holder or at such other place as the Holder hereof shall have designated to the Company in writing. Payment shall be credited
first to any costs, expenses or charges then payable to the Holder, then to accrued interest then due and payable, and then to principal.

 

2.2            Prepayment.
This Note may not be prepaid prior to the Maturity Date without the prior written consent of the Holder; provided, however, immediately
prior to, but conditioned upon, the consummation of a Sale of the Company, the Company may elect to prepay this Note in accordance with
the provisions set forth in Section 2.1 above.

 

3.            Conversion;
Payment upon Financing or Strategic Transaction.

 

3.1            Definitions.
The following terms shall have the respective meanings specified therefor below:

 

“Affiliate”
means, with respect to any specified Person, any other Person who or which, directly or indirectly, controls, or is controlled by, or
is under common control with such specified Person. For purposes of this definition, “control,” “controlled by”
and “under common control with” means the possession, directly or indirectly, of the power to direct or cause the direction
of the management and policies of a Person, whether through the ownership of voting securities, by contract or otherwise.

 

“Common Stock”
means the common stock, par value $0.001 per share, of the Company.

 

“Conversion Price”
means $1.48 (subject to appropriate adjustment in the event of any stock dividend, stock split, combination or similar recapitalization).

 

“Financing”
means any transaction or series of transactions, directly or indirectly, principally for capital raising purposes for the Company, including
the sale of equity, or the incurrence of indebtedness or the issuance of debt securities, or any combination thereof, other than a Sale
of the Company.

 

“Person”
means any individual, corporation, partnership, trust, limited liability company, association or other entity.

 

“Sale of the Company”
means the sale, lease, license, transfer or other disposition, directly or indirectly, of all or substantially all of the assets or intellectual
property, or a sale of a majority of the voting power, of the Company in a single transaction or series of related transactions (including
by way of merger, consolidation, stock sale or otherwise).

 

“Strategic Transaction”
means the sale, lease, license, transfer or other disposition, directly or indirectly, of any assets or intellectual property of the
Company, including the sale of royalties, in each case outside of the ordinary course of business (other than the Sale of the Company),
in a single transaction or series of related transactions.

 

    2

     

    

  

3.2            Maturity
Date Conversion. During the period beginning on the 30th day prior to the Maturity Date and ending on the day prior to
the Maturity Date (or the next business day if either of such days is not a business day), either the Company or the Holder may elect
to convert this Note into shares of Common Stock by providing written notice to the other party (the “Maturity Date Election
Notice”). In the event that neither the Company nor the Holder deliver such Maturity Date Election Notice, the Amount Due under
this Note shall become immediately due and payable on the Maturity Date. In the event that either the Company or the Holder deliver such
Maturity Date Election Notice, on the Maturity Date, this Note shall automatically, and without any further action of the Holder or the
Company, convert into a number of shares of Common Stock equal to the quotient obtained by dividing (i) the Amount Due on the date
of conversion by (ii) the Conversion Price, rounding down to the nearest whole number of shares.

 

3.3            Optional
Conversion; Payment upon Financing or Strategic Transaction. The Company covenants and agrees that it will provide written notice
to the Holder (a “Company Notice”) of the expected consummation of a Financing or Strategic Transaction. The Company
Notice shall describe the Financing or Strategic Transaction (as applicable) in reasonable detail, including the parties involved, the
terms and the anticipated date of closing of such transaction. The Company shall promptly revise the Company Notice and deliver it to
the Holder in the event of any material change to the information previously provided. The Financing or Strategic Transaction shall not
be consummated prior to the seventh (7th) day following Holder’s receipt of the last Company Notice (or revision thereto)
specifying the terms set forth above. The Company further covenants and agrees that from the period beginning on the delivery of the
Company Notice until the consummation of the Financing or Strategic Transaction, or the confirmation in writing by the Company that it
has abandoned pursuit of the Financing or Strategic Transaction, at the reasonable request of the Holder, the Company will meet with
the Holder and discuss the details of the Financing or Strategic Transaction from time to time. From the date of delivery of the Company
Notice until the date that is five (5) days prior to the consummation of the Financing or Strategic Transaction (the “Optional
Election Period”), the Holder may elect to convert this Note into shares of Common Stock by providing written notice to the
Company (an “Optional Election Notice”). To the extent that such Optional Election Notice is provided, this Note shall
convert into shares of Common Stock immediately prior to the consummation of the Financing or Strategic Transaction. The number of shares
of Common Stock to be issued upon such conversion shall be equal to the quotient obtained by dividing (i) the Amount Due on the
date of conversion by (ii) the Conversion Price, rounding down to the nearest whole number of shares. The Holder may elect to exercise
any Warrants (as defined below) issued pursuant to Section 3.4 prior to the consummation of the Financing or Strategic Transaction
and the Holder shall have all rights associated with the ownership of shares of Common Stock issued upon conversion of this Note or upon
exercise of any Warrant (including preemptive rights) in respect of the applicable Financing or Strategic Transaction. The Holder may
revoke any Optional Election Notice at any time prior to the consummation of the Financing or Strategic Transaction.

 

3.4            Issuance
of Warrants. Upon any conversion of this Note (whether on the Maturity Date, in connection with a Financing or Strategic Transaction
or following Shareholder Approval (as defined below), the Company shall issue and deliver warrants, in the form attached as Exhibit B
to the Purchase Agreement, to the Holder (collectively, the “Warrants”) entitling the Holder to acquire a number of
shares of Common Stock equal to the number of shares of Common Stock issued upon conversion of this Note, at a purchase price per share
equal to the Conversion Price in effect at the time of conversion.

 

    3

     

    

 

3.5            Conversion
Limitations. If the number of equity securities issuable upon conversion of this Note or exercise of the Warrants is limited by operation
of law without the approval of the holders of shares of Common Stock (including pursuant to Nasdaq Listing Rule 5635(d) or
any other rules or requirements of any stock exchange on which the securities of the Company are listed) (the “Stockholder
Approval”), the Company shall issue the maximum amount of equity securities issuable upon conversion of this Note or exercise
the Warrants absent such Shareholder Approval; it being understood that in connection with such partial conversion, the Company shall
issue an equal number of shares of Common Stock and Warrants. Following any such partial conversion, the remaining portion of this Note
will remain outstanding and the Company shall use reasonable best efforts to obtain the Stockholder Approval, including by calling a
meeting of stockholders to seek the Stockholder Approval, recommending that holders of shares of Common Stock vote in favor of the Shareholder
Approval and soliciting proxies in connection with such meeting. The Holder shall vote or cause to be voted the maximum number of shares
of Common Stock then owned by the Holder and that it is allowed to vote in accordance with applicable law or stock exchange requirements
in favor of any such Shareholder Approval; it being understood that in no event shall the Holder or its affiliates be required to exercise
any warrants (including the Warrants) or acquire any additional shares of Common Stock. Following the partial conversion of this Note
on the Maturity Date in accordance with Section 3.2, for so long as the Company continues to comply with its obligations in this
Section 3.5, the remaining Amount Due on the Note shall no longer accrue interest. To the extent that, and for so long that, the
Company ceases to comply with its obligations under this Section 3.5, interest shall accrue on the remaining Amount Due at the Default
Rate in accordance with the penultimate sentence of Section 1; provided that no such interest shall accrue if the Company ceases
to comply with this Section 3.5 due to the Holder’s failure to comply with its obligations hereunder. Upon receipt of such
Stockholder Approval, the remaining Amount Due under this Note may be converted into shares of Common Stock and Warrants equal to the
quotient obtained by dividing (i) the applicable remaining Amount Due by (ii) the Conversion Price then in effect, rounding
down to the nearest whole number of shares.

 

3.6            Fractional
Shares. No fractional shares of any of the Company’s equity securities will be issued in connection with any conversion of
this Note.

 

3.7            Certificate.
As promptly as practicable after the conversion of this Note, the Company at its expense will issue and deliver to the Holder, upon surrender
of this Note, a certificate or certificates for the number of full shares of Common Stock issuable upon such conversion.

 

4.            Demand;
Default. This Note shall, at the election of the Holder, become immediately due and payable, upon notice and demand by the Holder
(except in the case of clauses (a) through (d) below, which shall not require notice or demand), upon the occurrence of any
of the following events of default (individually, an “Event of Default” and collectively, “Events of Default”):

 

		(a)	the Company fails to make any payment
                                            when due under this Note on the applicable due date;

 

		(b)	the liquidation, dissolution or insolvency
                                            of the Company, or the appointment of a receiver, trustee, liquidator or custodian for the
                                            Company of a material part of its property;

 

    4

     

    

 

		(c)	the making of a general assignment by
                                            the Company or any subsidiary thereof for the benefit of its creditors;

 

		(d)	the Company’s breach of any of
                                            its material obligations under the Purchase Agreement or this Note;

 

		(e)	the
                                            Company or any subsidiary thereof becomes a debtor or alleged debtor in a case under the
                                            U.S. Bankruptcy Code or similar law or becomes the subject of any other bankruptcy or similar
                                            proceeding for the general adjustment of its debts or for its liquidation (whether on a voluntary
                                            or involuntary basis); or

 

		(f)	the Company’s Board of Directors
                                            or stockholders adopt a resolution for the liquidation, dissolution or winding up of the
                                            Company.

 

Upon the occurrence of any Event of Default,
all accrued but unpaid expenses, accrued but unpaid interest, all principal and any other amounts outstanding under this Note shall (i) in
the case of any Event of Default under Section 4(a), Section 4.(b), Section 4(c), or Section 4(e) hereof,
become immediately due and payable in full pursuant to the terms of Section 2.1 hereof without further notice, presentment,
demand, or protest of any kind by Holder, and (ii) in the case of any Event of Default pursuant to Section 4.1(d) hereof,
become immediately due and payable upon written notice by or on behalf of Holder to the Company after a thirty (30) day cure period is
given to the Company and such item has not been cured.

 

5.            No
Set-Off. All payments by the Company under this Note shall be made without set-off or counterclaim and be without any deduction or
withholding for any taxes or fees of any nature, unless the obligation to make such deduction or withholding is imposed by law.

 

6.            Seniority;
Security Interest. This Note shall be senior in all respects (including right of payment) to all other indebtedness of the Company
incurred subsequent to the issuance of this Note, and all other indebtedness of the Company incurred subsequent to the issuance of this
Note shall be expressly subordinated to this Note. The incurrence by the Company of any indebtedness subsequent to the issuance of this
Note not in compliance with this Section 6 shall be deemed an Event of Default. This Note will not be secured.

 

7.            General.

 

7.1            Transfers;
Successors and Assigns.

 

(i)            This
Note, and the obligations and rights of the parties hereunder, shall be binding upon and inure to the benefit of the Company, the holder
of this Note, and their respective heirs, successors and assigns; provided, however, that the Company may not transfer or assign its
obligations hereunder, by operation of law or otherwise, without the consent of the Holder; and provided further that the Holder may
not transfer or assign its rights hereunder, by operation of law of otherwise, except to an Affiliate, a direct or indirect equity holder
of Holder or a successor to all or a substantial portion of the assets of the assets of Holder, without the consent of the Company.

 

(ii)            Notwithstanding
anything else in this Note to the contrary, the right of any Holder (or transferee) to receive principal or interest payments under this
Note may be transferred only through the surrender of the current Note and reissuance of a new note by the Company pursuant to the provisions
of this paragraph. The foregoing language is intended to cause this Note to be in “registered form” as defined in Treasury
Regulations Sections 5f.103-1(c) and 1.871-14(c) and shall be interpreted and applied consistently therewith.

 

    5

     

    

 

7.2            No
Rights or Liabilities as Stockholder; No Personal Liability. Other than as set forth in the Definitive Documents, this Note does
not by itself entitle the Holder to any voting rights or other rights as a stockholder of the Company. In the absence of conversion of
this Note, no provisions of this Note, and no enumeration herein of the rights or privileges of the Holder, shall cause the Holder to
be a stockholder of the Company in respect of any of the Company’s equity securities which would be issued in connection with any
conversion of this Note. Holder agrees that no past, present or future stockholder, director, officer or employee of the Company shall
have any personal liability under the Securities Purchase Agreement or this Note for any claim based on, or in respect of, or by reason
of, such obligations or their creation and Holder waives and releases all such liability. Holder recognizes and agrees that such waiver
and release are part of the consideration for the issuance of the Note.

 

7.3            Further
Assurances. In the case of any conflict between this Note and the Securities Purchase Agreement, the provisions of the Securities
Purchase Agreement shall control and govern, except to the extent expressly provided herein. From time to time, the Holder and the Company
shall execute and deliver to the other party such additional documents as may reasonably be required to carry out the terms of this Note
and any agreements executed in connection herewith.

 

7.4            Amendment.
This Note may be amended or modified, or compliance with any term, covenant, agreement, condition or provision set forth herein may be
omitted or waived, either generally or in a particular instance, and either retroactively or prospectively, upon written consent of the
Company and the Holder.

 

7.5            Notices.
All notices and other communications given or made pursuant to this Agreement shall be in writing and shall be deemed effectively given
upon the earlier of actual receipt or: (a) personal delivery to the party to be notified, (b) when sent, if sent by electronic
mail during normal business hours of the recipient, and if not sent during normal business hours, then on the recipient’s next
business day, (c) five (5) days after having been sent by registered or certified mail, return receipt requested, postage prepaid,
or (d) one (1) business day after deposit with a nationally recognized overnight courier, freight prepaid, specifying next
business day delivery, with written verification of receipt. All communications shall be sent to the respective parties at their address
as set forth in Section 9.1 of the Securities Purchase Agreement, or to such e-mail address, facsimile number or address as subsequently
modified by written notice given in accordance with this Section 7.5. If notice is given to the Company, a copy shall also
be sent to Jack S. Bodner and Matthew C. Franker of Covington & Burling LLP at [***] and [***], respectively, which copy shall
not constitute notice.

 

 

7.6            Severability.
If one or more provisions of this Note are held to be invalid or unenforceable under applicable law, such provision shall be excluded
from this Note and the balance of this Note shall be interpreted as if such provision were so excluded and shall be enforceable in accordance
with its terms.

 

7.7            Governing
Law. This Note, any Warrants, and the obligations of the Company hereunder shall be governed by and interpreted and determined in
accordance with, the laws of the State of New York as to matters within the scope thereof, and as to all other matters shall be governed
by, and construed in accordance with, the internal laws of the State of New York (excluding the laws and rules of law applicable
to conflicts or choice of law).

 

[Signature on following page]

 

    6

     

    

 

IN WITNESS WHEREOF, this
Note has been duly executed on behalf of the undersigned on the day and in the year first written above.

 

	ENTASIS THERAPEUTICS HOLDINGS INC.	 
	 	 
	By:	  /s/
    Michael Gutch, Ph.D.	 
	Name:	Michael Gutch,
    Ph.D.	 
	Title:  	Chief Financial
    and Business Officer	 

 

Address:

c/o Entasis Therapeutics Holdings Inc. 

35 Gatehouse Drive 

Waltham, MA 02451

 

Acknowledged and agreed by Holder:

 

	INNOVIVA
    STRATEGIC OPPORTUNITIES LLC	 
	 	 
	By: 	/s/
    Pavel Raifeld	 
	Name:	Pavel Raifeld	 
	Title:	Chief Executive
    Officer	 

 

Address:

c/o Innoviva, Inc. 

1350 Old Bayshore Highway Suite 400 

Burlingame, CA 94010

 

[Signature Page to Convertible Promissory
Note]

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