Document:

Exhibit 10.14

 

TWENTY-FIFTH
LOAN MODIFICATION AGREEMENT

 

This
Twenty-fifth Loan Modification Agreement (this “Loan
Modification Agreement”) is entered into on the Twenty-fifth Loan
Modification Effective Date, by and between SILICON
VALLEY BANK, a California chartered bank, with its principal place
of business at 3003 Tasman Drive, Santa Clara, California 95054 and with a
loan production office located at One Newton Executive Park, Suite 200,
2221 Washington Street, Newton, Massachusetts 02462 (“Bank”)
and ASPEN TECHNOLOGY, INC., a
Delaware corporation with offices at 200 Wheeler Road, Burlington,
Massachusetts 01803 for itself and as successor by merger with ASPENTECH, INC., a Texas corporation with
offices at 200 Wheeler Road, Burlington, Massachusetts 01803 (“Borrower”).

 

1.                                       DESCRIPTION
OF EXISTING INDEBTEDNESS AND OBLIGATIONS. 
Among other indebtedness and obligations which may be owing by Borrower
to Bank, Borrower is indebted to Bank pursuant to a loan arrangement dated as
of January 30, 2003, evidenced by, among other documents,  a certain Loan and Security Agreement
dated as of January 30, 2003 between Borrower, Aspentech, Inc. and
Bank, as amended by a certain letter agreement dated February 14, 2003, a
certain First Loan Modification Agreement dated June 27, 2003, a certain
Second Loan Modification Agreement dated September 10, 2004, a certain
Third Loan Modification Agreement dated January 28, 2005, a certain Fourth
Loan Modification Agreement dated April 1, 2005, a certain Fifth Loan
Modification Agreement dated May 6, 2005, a certain Sixth Loan
Modification Agreement dated June 15, 2005, a certain Seventh Loan
Modification Agreement dated September, 2005, a certain Eighth Amendment to
Loan and Security Agreement dated November 22, 2005, a certain Ninth Loan
Modification Agreement dated July 17, 2006, a certain Tenth Loan
Modification Agreement dated September 15, 2006, a certain Eleventh Loan
Modification Agreement dated September 27, 2006, a certain Twelfth Loan
Modification Agreement dated January 12, 2007, a certain Thirteenth Loan
Modification Agreement dated April 13, 2007, a certain Fourteenth Loan
Modification Agreement dated June 28, 2007, a certain Waiver Agreement
dated June 28, 2007, a certain Fifteenth Loan Modification Agreement dated
August 30, 2007, a certain Sixteenth Loan Modification Agreement dated October 16,
2007, a certain Seventeenth Loan Modification Agreement dated December 28,
2007,  a certain Eighteenth Loan
Modification Agreement dated January 24, 2008, a certain Nineteenth Loan
Modification Agreement dated April 11, 2008, a certain Twentieth Loan
Modification Agreement dated May 15, 2008, a certain Twenty-first Loan
Modification Agreement dated June 13, 2008, a certain Twenty-second Loan
Modification Agreement dated July 15, 2008, a certain Twenty-third Loan
Modification Agreement, dated September 30, 2008, and a certain
Twenty-fourth Loan Modification Agreement, dated as of November 17, 2008 (as
amended, the “Loan Agreement”).  Capitalized terms used but not otherwise
defined herein shall have the same meaning as in the Loan Agreement.

 

2.                                       DESCRIPTION
OF COLLATERAL.  Repayment of the
Obligations is secured by the Collateral as described in the Loan Agreement
(together with any other collateral security granted to Bank, the “Security Documents”).

 

Hereinafter,
the Security Documents, together with all other documents evidencing or
securing the  Obligations shall be
referred to as the “Existing Loan Documents”.

 

3.                                       DESCRIPTION
OF CHANGE IN TERMS.

 

Modifications to Loan Agreement.

 

(i)                                    The
Loan Agreement shall be amended by deleting the following text appearing in Section 1.1
of the Loan Agreement:

 

“1.1  Loans.  Silicon will make loans to Borrower (the “Loans”),
up to the amounts (the “Credit Limit”) shown on the Schedule, provided no
Default or Event of Default has occurred and is continuing, and subject to
deduction of any Reserves for accrued interest and such other Reserves as
Silicon (upon prior written notice to Borrower setting forth 

 

 

the basis of such deduction) deems proper from time to
time.    Amounts borrowed may be repaid
and reborrowed during the term of this Agreement.”

 

and inserting in lieu thereof the following:

 

“1.1  Loans.  Silicon will make loans to Borrower (the “Loans”),
up to the amounts (the “Credit Limit”) shown on the Schedule, provided no
Default or Event of Default has occurred and is continuing, and subject to
deduction of any Reserves for accrued interest and such other Reserves as
Silicon (upon prior written notice to Borrower setting forth the basis of such
deduction) deems proper from time to time. 
Notwithstanding the foregoing, beginning on the Twenty-fifth Loan
Modification Effective Date and thereafter, Borrower shall provide Silicon not
less than five (5) Business Days’ prior written notice of any request for Loans
(other than Loans described in Section 1.5, Section 1.6 and Section 1.7
hereof).  Amounts borrowed may be repaid
and reborrowed during the term of this Agreement.”

 

(ii)                                 The
Loan Agreement shall be amended by deleting the following text appearing in Section 2
of the Schedule to the Loan Agreement:

 

“2. Interest.

 

Interest Rate (Section 1.2):

 

A rate equal to the “Prime Rate” in effect from time
to time, plus 0.5% per annum.  Interest
shall be calculated on the basis of a 360-day year for the actual number of
days elapsed. “Prime Rate” is the greater of (i) 4.25% or (ii) the
rate announced from time to time by Silicon as its “prime rate;” it is a base
rate upon which other rates charged by Silicon are based, and it is not
necessarily the best rate available at Silicon. 
The interest rate applicable to the Obligations shall change on each
date there is a change in the Prime Rate. 
Notwithstanding the foregoing, upon Borrower’s achievement of two
consecutive quarters of positive net income (as reasonably determined by
Silicon), the interest rate hereunder shall be reduced to the Prime Rate in
effect from time to time, plus zero percent (0.0%) per annum.  Such reduction in the interest rate shall be
effective five (5) business days after Silicon receives sufficient (in it
reasonable discretion) evidence of such achievement of positive net income.”

 

and inserting in lieu thereof the following:

 

“2. Interest.

 

Interest Rate (Section 1.2):

 

A rate equal to the “Prime Rate” in effect from time to
time, plus 0.5% per annum.  Interest
shall be calculated on the basis of a 360-day year for the actual number of
days elapsed. “Prime Rate” is the greater of (i) 4.25% or (ii) the
rate announced from time to time by Silicon as its “prime rate;” it is a base
rate upon which other rates charged by Silicon are based, and it is not
necessarily the best rate available at Silicon. 
The interest rate applicable to the Obligations shall change on each
date there is a change in the Prime Rate.”

 

(iii)                              The
Loan Agreement shall be amended by deleting the following text appearing in Section 4
of the Schedule to the Loan Agreement:

 

“MATURITY DATE

 

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(Section 6.1): January 15, 2009”

 

and inserting in lieu thereof the following:

 

 “MATURITY DATE

 

(Section 6.1): May 15, 2009”

 

(iv)                             The
Loan Agreement shall be amended by deleting the following text appearing in Section 5(b) of
the Schedule to the Loan Agreement:

 

“b. Minimum Cash or Excess Availability:

 

The Borrower shall at all times maintain $5,000,000.00
in (i) cash deposits maintained at Silicon, and/or (ii) excess “availability”
under this Agreement (net of Loans, Letters of Credit or other indebtedness
under this Agreement), as determined by Silicon based upon the Credit Limit
restrictions set forth in Section 1 above).”

 

and inserting in lieu thereof the following:

 

“b. Minimum Cash or Excess Availability:

 

The Borrower shall at all times maintain $75,000,000.00
in (i) cash deposits maintained at Silicon, and/or (ii) excess “availability”
under this Agreement (net of Loans, Letters of Credit or other indebtedness
under this Agreement), as determined by Silicon based upon the Credit Limit
restrictions set forth in Section 1 above).”

 

(v)                                The
Loan Agreement shall be amended by deleting the following text at the end of Section 6(1) of
the Schedule to the Loan Agreement:

 

“1.           From
the date hereof through June 30, 2003, weekly and upon each loan request,
borrowing base certificates.  From July 1,
2003 and thereafter, weekly and upon each loan request, borrowing base
certificates and transaction reports. 
Notwithstanding the foregoing, (i) if Borrower is on “non-borrowing
reporting status” and maintains at least $10,000,000 in cash on deposit at
Silicon and/or excess “availability” hereunder, such reports shall be due
bi-weekly and (ii) if Borrower is on “non-borrowing reporting status” and
maintains at least $20,000,000 in cash on deposit at Silicon and/or excess “availability”
hereunder, such reports shall be due monthly; provided further, however, in all
instances, Borrower shall not be required to deliver transaction reports to
Bank during the period commencing August 1, 2007 through August 15,
2008; provided, further, that beginning on the Twenty-third Loan Modification Effective
Date through the Maturity Date, Bank waives receipt of borrowing base
certificates and transaction reports otherwise deliverable hereunder.  Bank hereby waives delivery by Borrower of
any such certificates or reports previously required hereunder but not
delivered.”

 

and inserting in lieu thereof the following:

 

“1.           Through
June 30, 2003, weekly and upon each loan request, borrowing base
certificates.  From July 1, 2003 and
thereafter, weekly and upon each loan request, borrowing base certificates and
transaction reports.  Notwithstanding the
foregoing, (i) if Borrower is on “non-borrowing reporting status” and
maintains at least $10,000,000 in cash on deposit at Silicon and/or excess “availability”
hereunder, such reports shall be due bi-weekly and (ii) if Borrower is on “non-borrowing
reporting status” and maintains at least $20,000,000 in cash on deposit at
Silicon and/or excess “availability” hereunder, such reports shall be due
monthly; provided  further, however, in all instances, Borrower 

 

3

 

shall not be required to deliver transaction reports
to Bank during the period commencing August 1, 2007 through August 15,
2008; provided, further, that beginning on the Twenty-third Loan
Modification Effective Date through November 30, 2008, Bank waives receipt
of borrowing base certificates and transaction reports otherwise deliverable
hereunder.  Bank hereby further waives
delivery by Borrower of any such certificates or reports previously required
hereunder through the reporting period ended November 30, 2008 but not
delivered.  Notwithstanding the
foregoing, (i) with respect to the monthly period ending December 31,
2008, Borrower shall deliver its borrowing base certificate and transaction
report on or before February 15, 2009 and (ii) commencing with the
monthly period ending January 31, 2009, Borrower shall deliver monthly,
within thirty (30) days after the end of each month, and upon each Loan request
or any other request for a credit extension, borrowing base certificates and
transaction reports.”

 

(vi)                             The
Loan Agreement shall be amended by deleting the following text appearing in Section 6(2) of
the Schedule to the Loan Agreement:

 

“2.           Monthly
accounts payable agings, aged by invoice date, and outstanding or held check
registers, if any, within twenty days after the end of each month; provided,
however, Borrower shall not be required to deliver its monthly accounts payable
agings to Bank during the period commencing November 1, 2007 through August 15,
2008 (reporting will be due as scheduled commencing with the period ending July 31,
2008); provided, further, that beginning on the Twenty-third Loan Modification
Effective Date through the Maturity Date, Bank waives receipt of monthly
accounts payable agings, aged by invoice date, and outstanding or held check
registers otherwise deliverable hereunder. Bank hereby waives delivery by
Borrower of any such agings or held check registers previously required
hereunder but not delivered.”

 

and inserting in lieu thereof the following:

 

“2.           Monthly
accounts payable agings, aged by invoice date, and outstanding or held check
registers, if any, within twenty (20) days after the end of each month; provided,
however, Borrower shall not be required to deliver its monthly accounts
payable agings to Bank during the period commencing November 1, 2007
through August 15, 2008 (reporting will be due as scheduled commencing
with the period ending July 31, 2008); provided, further,
that beginning on the Twenty-third Loan Modification Effective Date through November 30,
2008, Bank waives receipt of monthly accounts payable agings, aged by invoice
date, and outstanding or held check registers otherwise deliverable hereunder.
Bank hereby further waives delivery by Borrower of any such agings or held
check registers previously required hereunder through the reporting period
ended November 30, 2008 but not delivered. 
Notwithstanding the foregoing, (i) with respect to the monthly reporting
period ending December 31, 2008, Borrower shall deliver its monthly
accounts payable agings, aged by invoice date, and outstanding or held check
registers, if any, on or before February 15, 2009 and (ii) commencing
with the monthly reporting period ending January 31, 2009, monthly
accounts payable agings, aged by invoice date, and outstanding or held check
registers, if any, within thirty (30) days after the end of each month.”

 

(vii)                          The Loan
Agreement shall be amended by deleting the following text appearing in Section 6(3) of
the Schedule to the Loan Agreement:

 

“3.           Monthly
Receivable agings, aged by invoice date, and receivable reconciliations, within
twenty days after the end of each month; provided, however, Borrower shall not
be required to deliver its monthly Receivable agings to Bank during the period
commencing November 1, 2007 through August 15, 2008 (reporting will
be due as scheduled commencing with the period ending July 31, 2008);
provided, further, 

 

4

 

that beginning on the Twenty-third Loan Modification
Effective Date through the Maturity Date, Bank waives receipt of monthly
Receivable agings and receivable reconciliations otherwise deliverable
hereunder.  Bank hereby waives delivery
by Borrower of any such agings and reconciliations previously required
hereunder but not delivered.”

 

and inserting in lieu thereof the following:

 

“3.           Monthly
Receivable agings, aged by invoice date, and receivable reconciliations, within
twenty (20) days after the end of each month; provided, however,
Borrower shall not be required to deliver its monthly Receivable agings to Bank
during the period commencing November 1, 2007 through August 15, 2008
(reporting will be due as scheduled commencing with the period ending July 31,
2008); provided, further, that beginning on the Twenty-third Loan
Modification Effective Date through November 30, 2008, Bank waives receipt
of monthly Receivable agings and receivable reconciliations otherwise
deliverable hereunder.  Bank hereby further
waives delivery by Borrower of any such agings and reconciliations previously
required hereunder through the reporting period ended November 30, 2008 but
not delivered.  Notwithstanding the
foregoing, (i) with respect to the monthly reporting period ending December 31,
2008, Borrower shall deliver its monthly accounts Receivable agings, aged by
invoice date, and receivable reconciliations, on or before February 15,
2009 and (ii) commencing with the monthly reporting period ending January 31,
2009, monthly Receivable agings, aged by invoice date, and receivable
reconciliations, within thirty (30) days after the end of each month.”

 

(viii)                       The Loan
Agreement shall be amended by deleting the following text appearing in Section 6(4) of
the Schedule to the Loan Agreement:

 

“4.           Monthly
unaudited financial statements, as soon as available, and in any event within
thirty days after the end of each month; provided, however,  Bank
hereby waives receipt of Borrower’s monthly unaudited financial statements
effective for each of the monthly periods ending April 30, 2007 through
and including the Maturity Date.”

 

and inserting in lieu thereof the following:

 

“4.           Monthly
unaudited financial statements, as soon as available, and in any event within
thirty (30) days after the end of each month; provided, however,  Bank hereby waives receipt of Borrower’s monthly unaudited
financial statements effective for each of the monthly periods ending April 30,
2007 through and including the monthly period ending March 31, 2009.”

 

(ix)                               The
Loan Agreement shall be amended by deleting the following text at the end of Section 6(5) of
the Schedule to the Loan Agreement:

 

“5.           Monthly
Compliance Certificates, within thirty days after the end of each month, in
such form as Silicon shall reasonably specify, signed by the Chief Financial
Officer of Borrower, certifying that as of the end of such month Borrower was
in full compliance with all of the terms and conditions of this Agreement, and
setting forth calculations showing compliance with the financial covenants set
forth in this Agreement and such other information as Silicon shall reasonably
request, including, without limitation, a statement that at the end of such
month there were no held checks; provided, however, (i) Borrower may in
lieu thereof deliver its monthly Compliance Certificates for the period ending
on a date between April 30, 2007 and November 30, 2007, inclusive, in
draft form, provided further that Borrower delivers its monthly Compliance
Certificates for the periods ending on June 30, 2007 and September 30,
2007 in final form, as soon as 

 

5

 

available, and in any event no later than May 15,
2008, (ii) Borrower may deliver its monthly Compliance Certificate for the
periods ending December 31, 2007 and March 31, 2008, in draft form,
as soon as available, and in any event no later than April 9, 2008, with
final forms to be delivered to Bank as soon as available but in no event later
than August 29, 2008, (iii) Borrower may deliver its monthly
Compliance Certificate for the period ending March 31, 2008, in draft
form, as soon as available, and in any event no later than June 15, 2008,
with final forms to be delivered to Bank as soon as available but in no event
later than August 29, 2008, and (iv) Borrower may deliver its monthly
Compliance Certificate for the period ended June 30, 2008, as soon as
available but in no event later than September 15, 2008.  Bank hereby waives (i) receipt of
Borrower’s monthly Compliance Certificates (x) for the periods ending October 31,
2007, November 30, 2007, January 31, 2008, February 29, 2008, April 30,
2008, May 31, 2008, July 31, 2008, August 31, 2008 and October 31,
2008 and (y) receipt of Borrower’s monthly Compliance Certificate for the
period ending December 31, 2007, in draft form, on or before January 31,
2008; provided, further, that beginning on the Twenty-third Loan Modification
Effective Date, Borrower may in lieu thereof deliver its monthly Compliance
Certificates for the monthly period coinciding with each fiscal quarter end of
the Borrower (each September 30, December 31, March 31, and June 30),
within five (5) days of filing the quarterly financials of the Borrower
pursuant to Section 6(6) for such fiscal quarter with the SEC.  Bank hereby waives delivery of all other
monthly Compliance Certificates; provided, further, that beginning on the
Twenty-fourth Loan Modification Effective Date through the Maturity Date, Bank
waives receipt of all monthly Compliance Certificates otherwise deliverable
hereunder.  Notwithstanding the foregoing,
Borrower shall promptly deliver such information as Bank shall reasonably
request to enable Bank to verify Borrower’s compliance with the financial
covenants contained in Section 5 of the Schedule to the Loan Agreement.”

 

and inserting in lieu thereof the following:

 

“5.           Monthly
Compliance Certificates, within thirty (30) days after the end of each month,
in such form as Silicon shall reasonably specify, signed by the Chief Financial
Officer of Borrower, certifying that as of the end of such month Borrower was
in full compliance with all of the terms and conditions of this Agreement, and
setting forth calculations showing compliance with the financial covenants set
forth in this Agreement and such other information as Silicon shall reasonably
request, including, without limitation, a statement that at the end of such
month there were no held checks; provided, however, (i) Borrower
may in lieu thereof deliver its monthly Compliance Certificates for the period
ending on a date between April 30, 2007 and November 30, 2007,
inclusive, in draft form, provided  further that Borrower may deliver
its monthly Compliance Certificates for the periods ending on June 30,
2007 and September 30, 2007 in final form, as soon as available, and in
any event no later than May 15, 2008, (ii) Borrower may deliver its
monthly Compliance Certificate for the periods ending December 31, 2007
and March 31, 2008, in draft form, as soon as available, and in any event
no later than June 15, 2008, with final forms to be delivered to Bank as
soon as available but in no event later than February 15, 2009, and (iii) Borrower
may deliver its monthly Compliance Certificate for the period ended June 30,
2008 as soon as available but in no event later than April 30, 2009 and its
monthly Compliance Certificate for the period ended September 30, 2008, as
soon as available but in no event later than  May 15, 2009.  Bank hereby waives receipt of Borrower’s
monthly Compliance Certificates (x) for the periods ending October 31,
2007, November 30, 2007, January 31, 2008, February 29, 2008, April 30,
2008, May 31, 2008, July 31, 2008, August 31, 2008 and October 31,
2008 and (y) receipt of Borrower’s monthly Compliance Certificate for the
period ending December 31, 2007, in draft form, on or before January 31,
2008; provided, further, that Borrower shall not be required to
deliver the monthly Compliance Certificates otherwise required hereunder for
the monthly periods ending November 30, 2008, January 31, 2009 

 

6

 

and February 28, 2009 and Borrower may deliver
its monthly Compliance Certificates for the monthly period coinciding with the
fiscal quarters ending December 31, 2008 and March 31, 2009 within
five (5) days of filing the quarterly financial statements of the Borrower
pursuant to Section 6(6) for such fiscal quarter with the SEC.  Notwithstanding the foregoing, Borrower shall
promptly deliver such information as Bank shall reasonably request to enable
Bank to verify Borrower’s compliance with the financial covenants contained in Section 5
of the Schedule to the Loan Agreement.”

 

(x)                                  The
Loan Agreement shall be amended by deleting the following text appearing in Section 6(6) of
the Schedule to the Loan Agreement:

 

“6.           Quarterly
unaudited financial statements, as soon as available, and in any event within
forty-five days after the end of each fiscal quarter of Borrower; provided,
however, Borrower may in lieu thereof (i) deliver its quarterly unaudited
financial statements for the periods ending on June 30, 2007, September 30,
2007 and December 31, 2007 in draft form as soon as available, and in any
event no later than April 9, 2008, with final forms of the September 30,
2007 quarterly unaudited financial statements to be delivered to Bank within
three days of the filing of such financial statements with the SEC but in no
event later than May 15, 2008; (ii) deliver its quarterly unaudited
financial statements for the period ending on December 31, 2007 in final
form within three days of the filing of such financial statements with the SEC
but in no event later than August 29, 2008; (iii) deliver its
quarterly unaudited financial statements for the period ending on March 31,
2008 to Bank within three days of the filing of such financial statements with
the SEC but in no event later than August 29, 2008; and (iv) deliver
its quarterly unaudited financial statements for the period ended June 30,
2008 to Bank within three days of the filing of such financial statements with
the SEC but in no event later than September 15, 2008.  Bank hereby waives receipt of Borrower’s
quarterly unaudited financial statement for the period ending December 31,
2007 in draft form on or before February 15, 2008; provided, further, that
beginning on the Twenty-third Loan Modification Effective Date, Borrower may in
lieu thereof deliver its quarterly unaudited financial statements to Bank
contemporaneously with the filing of such quarterly financial statements with
the SEC.”

 

and inserting in lieu thereof the following:

 

“6.           As
soon as available, and in any event within the earlier to occur of (X) forty-five
(45) days after the end of each fiscal quarter of Borrower and (Y) five (5) days
of filing its quarterly report with the SEC (including, without limitation, SEC
Form 10-Q), quarterly unaudited financial statements; provided, however,
Borrower may (i) deliver its quarterly unaudited financial statements for
the periods ending on June 30, 2007 and September 30, 2007 in draft
form as soon as available, and in any event no later than April 9, 2008,
with final forms of the September 30, 2007 quarterly unaudited financial
statements to be delivered to Bank within three (3) days of the filing of
such financial statements with the SEC but in no event later than May 15,
2008; (ii) file its quarterly report with the SEC (including, without
limitation, SEC Form 10-Q), for the quarterly periods ended December 31,
2007 and March 31, 2008 as soon as available, and in any event on or
before February 15, 2009; (iii) file its quarterly report with the
SEC (including, without limitation, SEC Form 10-Q), for the quarterly
periods ended September 30, 2008, December 31, 2008 and March 31,
2009 as soon as available, and in any event on or before May 15, 2009. “

 

(xi)                               The
Loan Agreement shall be amended by deleting the following text appearing in Section 6(8) of
the Schedule to the Loan Agreement:

 

7

 

“8.           Annual
financial statements, as soon as available, and in any event within 120 days
following the end of Borrower’s fiscal year, certified by independent certified
public accountants acceptable to Silicon, together with an unqualified opinion
on the financial statements; provided, however, Borrower may in lieu thereof
deliver its annual financial statements for the period ending on June 30,
2007 as soon as available, and in any event within three days of the filing of
such financial statements with the SEC but in no event later than May 15,
2008; provided, further, that beginning on the Twenty-third Loan Modification
Effective Date, Borrower may in lieu thereof deliver its annual financial
statements to Bank contemporaneously with the filing of such annual financial
statements with the SEC.”

 

and inserting in lieu thereof the following:

 

“8.           As
soon as available, and in any event within the earlier to occur of (X) one
hundred twenty (120) days after the end of Borrower’s fiscal year and (Y) five
(5) days of filing its annual financial statements with the SEC
(including, without limitation, SEC Form 10-K), annual financial
statements, certified by independent certified public accountants acceptable to
Silicon, together with an unqualified opinion on the financial statements; provided,
however, Borrower may deliver its annual financial statements for the annual
period ended June 30, 2007 as soon as available, and in any event within
three days of the filing of such financial statements with the SEC but in no
event later than May 15, 2008; provided, further,  however,
Borrower may file its annual report with the SEC (including, without
limitation, SEC Form 10-K) for the annual period ended June 30, 2008
as soon as available, and in any event on or before April 30, 2009.”

 

(xii)                          The Loan
Agreement shall be amended by inserting the following text at the end of Section 8(1) of
the Schedule to the Loan Agreement:

 

“(f) The
foregoing depository requirements are in addition to and supplemental of the financial
covenants contained in Section 5 of the Schedule to the Loan Agreement.”

 

(xiii)                       Section 8
of the Loan Agreement shall be amended by adding the following definitions
thereto, each in the appropriate alphabetical order:

 

““Twenty-fifth Loan Modification Agreement”
means that certain Twenty-fifth Loan Modification Agreement, executed on the
Twenty-fifth Loan Modification Effective Date.

 

“Twenty-fifth Loan Modification Effective Date”
means the date indicated on the signature page to the Twenty-fifth Loan
Modification Agreement.”

 

4.                                       FEES.  Borrower shall pay to Bank an extension fee
of Eighty Thousand Dollars ($80,000.00), which fee shall be due on the date
hereof and shall be deemed fully earned as of the date hereof.  Borrower shall also reimburse Bank for all
legal fees and expenses incurred in connection with this amendment to the Existing
Loan Documents.

 

5.                                       RATIFICATION
OF NEGATIVE PLEDGE.  Borrower hereby
ratifies, confirms and reaffirms, all and singular, the terms and conditions of
a certain Negative Pledge Agreements each dated as of January 30, 2003
between Borrower and Bank, and acknowledges, confirms and agrees that said
Negative Pledge Agreement  shall remain
in full force and effect.

 

6.                                       RATIFICATION
OF PERFECTION CERTIFICATES.  Borrower
hereby ratifies, confirms and reaffirms, all and singular, the terms and
disclosures contained in certain Perfection Certificates each dated as of January 30,
2003, as amended and affected by Schedule 1 to the Fourth Amendment and Exhibit A
to the Fourth Amendment and acknowledges, confirms and agrees the disclosures
and 

 

8

 

information therein, in
Schedule 3.10 to the Loan Agreement, in Schedule 1 annexed to the Tenth Loan
Modification Agreement, and/or in connection with the formation of subsidiaries
as contemplated by the Guggenheim Transactions and the Key Transactions (as defined
in the Sixth Loan Modification Agreement and the Eleventh Loan Modification
Agreement, respectively), have not changed as of the date hereof.

 

7.                                       CONSISTENT
CHANGES.  The Existing Loan Documents
are hereby amended wherever necessary to reflect the changes described above.

 

8.                                       RATIFICATION
OF LOAN DOCUMENTS.  Borrower hereby
ratifies, confirms, and reaffirms all terms and conditions of all security or
other collateral granted to the Bank and confirms that the indebtedness secured
thereby includes, without limitation, the Obligations.

 

9.                                       NO
DEFENSES OF BORROWER.  Borrower
hereby acknowledges and agrees that Borrower has no offsets, defenses, claims,
or counterclaims against Bank with respect to the Obligations, or otherwise,
and that if Borrower now has, or ever did have, any offsets, defenses, claims,
or counterclaims against Bank, whether known or unknown, at law or in equity,
all of them are hereby expressly WAIVED and Borrower hereby RELEASES Bank from
any liability thereunder.

 

10.                                 CONTINUING
VALIDITY.  Borrower understands and
agrees that in modifying the existing Obligations, Bank is relying upon
Borrower’s representations, warranties, and agreements, as set forth in the
Existing Loan Documents, after giving effect to this Loan Modification
Agreement and the Waiver Agreement entered into between Borrower and Bank dated
as of the date hereof.  Except as
expressly modified pursuant to this Loan Modification Agreement, the terms of
the Existing Loan Documents remain unchanged and in full force and effect.  Bank’s agreement to modifications to the
existing Obligations pursuant to this 
Loan Modification Agreement in no way shall obligate Bank to make any
future modifications to the Obligations. 
Nothing in this Loan Modification Agreement shall constitute a
satisfaction of the Obligations.  It is
the intention of Bank and Borrower to retain as liable parties all makers of
Existing Loan Documents, unless the party is expressly released by Bank in
writing.

 

11.                                 COUNTERSIGNATURE.  This Loan Modification Agreement shall become
effective only when it shall have been executed by Borrower and Bank.

 

[Remainder of page intentionally
left blank.]

 

9

 

This
Loan Modification Agreement is executed as a sealed instrument under the laws
of the Commonwealth of Massachusetts as of the Twenty-fifth Loan Modification
Effective Date.

 

	
   

  	
  BORROWER:

  
	
   

  	
   

  
	
   

  	
  ASPEN
  TECHNOLOGY, INC.

  
	
   

  	
   

  
	
   

  	
   

  
	
   

  	
  By:

  	
  /s/ Bradley T. Miller

  
	
   

  	
  Name:

  	
  Bradley T.
  Miller

  
	
   

  	
  Title:

  	
  Chief Financial
  Officer

  
	
   

  	
   

  
	
   

  	
  BANK:

  
	
   

  	
   

  
	
   

  	
  SILICON VALLEY
  BANK

  
	
   

  	
   

  
	
   

  	
   

  
	
   

  	
  By:

  	
  /s/ Michael Tramack

  
	
   

  	
  Name:

  	
  Michael Tramack

  
	
   

  	
  Title:

  	
  Senior
  Vice President

  

 

 

Twenty-fifth Loan
Modification Effective Date: January 15, 2009.

 

 

[Twenty-fifth Loan
Modification Agreement Signature Page]Exhibit 4.1

 

UST No. 494

 

WARRANT TO PURCHASE PREFERRED STOCK

 

THE SECURITIES REPRESENTED BY THIS INSTRUMENT HAVE NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR THE SECURITIES LAWS
OF ANY STATE AND MAY NOT BE TRANSFERRED, SOLD OR OTHERWISE DISPOSED OF
EXCEPT WHILE A REGISTRATION STATEMENT RELATING THERETO IS IN EFFECT UNDER SUCH
ACT AND APPLICABLE STATE SECURITIES LAWS OR PURSUANT TO AN EXEMPTION FROM
REGISTRATION UNDER SUCH ACT OR SUCH LAWS. 
THIS INSTRUMENT IS ISSUED SUBJECT TO THE RESTRICTIONS ON TRANSFER AND
OTHER PROVISIONS OF A SECURITIES PURCHASE AGREEMENT BETWEEN THE ISSUER OF THESE
SECURITIES AND THE INVESTOR REFERRED TO THEREIN, A COPY OF WHICH IS ON FILE
WITH THE ISSUER. THE SECURITIES REPRESENTED BY THIS INSTRUMENT MAY NOT BE
SOLD OR OTHERWISE TRANSFERRED EXCEPT IN COMPLIANCE WITH SAID AGREEMENT.  ANY SALE OR OTHER TRANSFER NOT IN COMPLIANCE
WITH SAID AGREEMENT WILL BE VOID.

 

WARRANT

to purchase

50.00050

Shares of Preferred Stock

 

of BankGreenville
Financial Corporation

 

Issue
Date:  February 13, 2009

 

1.                                       Definitions. Unless
the context otherwise requires, when used herein the following terms shall have
the meanings indicated.

 

“Board of
Directors” means the board of directors of the Company, including
any duly authorized committee thereof.

 

“business
day” means any day except Saturday, Sunday and any day on which
banking institutions in the State of New York generally are authorized or
required by law or other governmental actions to close.

 

“Charter”
means, with respect to any Person, its certificate or articles of
incorporation, articles of association, or similar organizational document.

 

“Company”
means the Person whose name, corporate or other organizational form and
jurisdiction of organization is set forth in Item 1 of Schedule A hereto.

 

“Exchange
Act” means the Securities Exchange Act of 1934, as amended, or any 

 

1

 

successor statute, and the rules and
regulations promulgated thereunder.

 

“Exercise
Price” means the amount set forth in Item 2 of Schedule A hereto.

 

“Expiration
Time” has the meaning set forth in Section 3.

 

“Issue
Date” means the date set forth in Item 3 of Schedule A hereto.

 

“Liquidation
Amount” means the amount set forth in Item 4 of Schedule A hereto.

 

“Original
Warrantholder” means the United States Department of the
Treasury.  Any actions specified to be
taken by the Original Warrantholder hereunder may only be taken by such Person
and not by any other Warrantholder.

 

“Person”
has the meaning given to it in Section 3(a)(9) of the Exchange Act
and as used in Sections 13(d)(3) and 14(d)(2) of the Exchange Act.

 

“Preferred
Stock” means the series of perpetual preferred stock set forth in Item 5 of
Schedule A hereto.

 

“Purchase
Agreement” means the Securities Purchase Agreement — Standard Terms
incorporated into the Letter Agreement, dated as of the date set forth in Item
6 of Schedule A hereto, as amended from time to time, between the Company and
the United States Department of the Treasury (the “Letter Agreement”), including all annexes and schedules
thereto.

 

“Regulatory
Approvals” with respect to the Warrantholder, means, to the extent
applicable and required to permit the Warrantholder to exercise this Warrant
for shares of Preferred Stock and to own such Preferred Stock without the
Warrantholder being in violation of applicable law, rule or regulation,
the receipt of any necessary approvals and authorizations of, filings and
registrations with, notifications to, or expiration or termination of any
applicable waiting period under, the Hart-Scott-Rodino Antitrust Improvements
Act of 1976, as amended, and the rules and regulations thereunder.

 

“SEC”
means the U.S. Securities and Exchange Commission.

 

“Securities
Act” means the Securities Act of 1933, as amended, or any successor
statute, and the rules and regulations promulgated thereunder.

 

“Shares”
has the meaning set forth in Section 2.

 

“Warrantholder”
has the meaning set forth in Section 2.

 

“Warrant”
means this Warrant, issued pursuant to the Purchase Agreement.

 

2.                                       Number of Shares; Exercise Price. This certifies that, for value received, the United States
Department of the Treasury or its permitted assigns (the “Warrantholder”) is entitled, upon the
terms and subject to the conditions hereinafter set forth, to acquire from the
Company, in whole or in part, after the receipt of all applicable Regulatory
Approvals, if any, up to an aggregate of the 

 

2

 

number of fully paid and nonassessable shares of Preferred
Stock set forth in Item 7 of Schedule A hereto (the “Shares”), at a purchase price per share of Preferred Stock
equal to the Exercise Price.

 

3.                                       Exercise of Warrant; Term.
Subject to Section 2, to the extent permitted by applicable laws and
regulations, the right to purchase the Shares represented by this Warrant is
exercisable, in whole or in part by the Warrantholder, at any time or from time
to time after the execution and delivery of this Warrant by the Company on the
date hereof, but in no event later than 5:00 p.m., New York City time on
the tenth anniversary of the Issue Date (the “Expiration
Time”), by (A) the surrender of this Warrant and Notice of
Exercise annexed hereto, duly completed and executed on behalf of the
Warrantholder, at the principal executive office of the Company located at the
address set forth in Item 8 of Schedule A hereto (or such other office or
agency of the Company in the United States as it may designate by notice in
writing to the Warrantholder at the address of the Warrantholder appearing on
the books of the Company), and (B) payment of the Exercise Price for the
Shares thereby purchased, by having the Company withhold, from the shares of
Preferred Stock that would otherwise be delivered to the Warrantholder upon
such exercise, shares of Preferred Stock issuable upon exercise of the Warrant
with an aggregate Liquidation Amount equal in value to the aggregate Exercise
Price as to which this Warrant is so exercised.

 

If the Warrantholder does not exercise this
Warrant in its entirety, the Warrantholder will be entitled to receive from the
Company within a reasonable time, and in any event not exceeding three business
days, a new warrant in substantially identical form for the purchase of that
number of Shares equal to the difference between the number of Shares subject
to this Warrant and the number of Shares as to which this Warrant is so
exercised.  Notwithstanding anything in
this Warrant to the contrary, the Warrantholder hereby acknowledges and agrees
that its exercise of this Warrant for Shares is subject to the condition that
the Warrantholder will have first received any applicable Regulatory Approvals.

 

4.                                       Issuance of Shares; Authorization. Certificates for Shares issued upon exercise of this
Warrant will be issued in such name or names as the Warrantholder may designate
and will be delivered to such named Person or Persons within a reasonable time,
not to exceed three business days after the date on which this Warrant has been
duly exercised in accordance with the terms of this Warrant.  The Company hereby represents and warrants
that any Shares issued upon the exercise of this Warrant in accordance with the
provisions of Section 3 will be duly and validly authorized and issued,
fully paid and nonassessable and free from all taxes, liens and charges (other
than liens or charges created by the Warrantholder, income and franchise taxes
incurred in connection with the exercise of the Warrant or taxes in respect of
any transfer occurring contemporaneously therewith).  The Company agrees that the Shares so issued
will be deemed to have been issued to the Warrantholder as of the close of
business on the date on which this Warrant and payment of the Exercise Price
are delivered to the Company in accordance with the terms of this Warrant,
notwithstanding that the stock transfer books of the Company may then be closed
or certificates representing such Shares may not be actually delivered on such
date. The Company will at all times reserve and keep available, out of its
authorized but unissued preferred stock, solely for the purpose of providing
for the exercise of this Warrant, the aggregate number of shares of Preferred
Stock then issuable upon exercise of this Warrant at any time.  The Company will use reasonable best efforts
to ensure that the Shares may be issued without violation of any applicable law
or regulation or of any requirement of any securities exchange on which the
Shares are listed or traded.

 

3

 

5.                                       No Rights as Stockholders; Transfer Books. This Warrant does not entitle the Warrantholder to any
voting rights or other rights as a stockholder of the Company prior to the date
of exercise hereof. The Company will at no time close its transfer books
against transfer of this Warrant in any manner which interferes with the timely
exercise of this Warrant.

 

6.                                       Charges, Taxes and Expenses.
Issuance of certificates for Shares to the Warrantholder upon the exercise of
this Warrant shall be made without charge to the Warrantholder for any issue or
transfer tax or other incidental expense in respect of the issuance of such
certificates, all of which taxes and expenses shall be paid by the Company.

 

7.                                       Transfer/Assignment.

 

(A) Subject to compliance with clause (B) of
this Section 7, this Warrant and all rights hereunder are transferable, in
whole or in part, upon the books of the Company by the registered holder hereof
in person or by duly authorized attorney, and a new warrant shall be made and
delivered by the Company, of the same tenor and date as this Warrant but
registered in the name of one or more transferees, upon surrender of this
Warrant, duly endorsed, to the office or agency of the Company described in Section 3.  All expenses (other than stock transfer
taxes) and other charges payable in connection with the preparation, execution
and delivery of the new warrants pursuant to this Section 7 shall be paid
by the Company.

 

(B) The transfer of the Warrant and the Shares
issued upon exercise of the Warrant are subject to the restrictions set forth
in Section 4.4 of the Purchase Agreement. 
If and for so long as required by the Purchase Agreement, this Warrant
shall contain the legends as set forth in Section 4.2(a) of the
Purchase Agreement.

 

8.                                       Exchange and Registry of Warrant. This Warrant is exchangeable, upon the surrender hereof by
the Warrantholder to the Company, for a new warrant or warrants of like tenor
and representing the right to purchase the same aggregate number of
Shares.  The Company shall maintain a
registry showing the name and address of the Warrantholder as the registered
holder of this Warrant. This Warrant may be surrendered for exchange or
exercise in accordance with its terms, at the office of the Company, and the
Company shall be entitled to rely in all respects, prior to written notice to
the contrary, upon such registry.

 

9.                                       Loss, Theft, Destruction or Mutilation of Warrant. Upon receipt by the Company of evidence reasonably
satisfactory to it of the loss, theft, destruction or mutilation of this
Warrant, and in the case of any such loss, theft or destruction, upon receipt
of a bond, indemnity or security reasonably satisfactory to the Company, or, in
the case of any such mutilation, upon surrender and cancellation of this
Warrant, the Company shall make and deliver, in lieu of such lost, stolen,
destroyed or mutilated Warrant, a new Warrant of like tenor and representing
the right to purchase the same aggregate number of Shares as provided for in
such lost, stolen, destroyed or mutilated Warrant.

 

10.                                 Saturdays, Sundays, Holidays, etc. If the last or appointed day for the taking of any action or
the expiration of any right required or granted herein shall not be a business
day, then such action may be taken or such right may be exercised on the next
succeeding day that is a business day.

 

4

 

11.                                 Rule 144 Information.
The Company covenants that it will use its reasonable best efforts to timely
file all reports and other documents required to be filed by it under the
Securities Act and the Exchange Act and the rules and regulations
promulgated by the SEC thereunder (or, if the Company is not required to file
such reports, it will, upon the request of any Warrantholder, make publicly
available such information as necessary to permit sales pursuant to Rule 144
under the Securities Act), and it will use reasonable best efforts to take such
further action as any Warrantholder may reasonably request, in each case to the
extent required from time to time to enable such holder to, if permitted by the
terms of this Warrant and the Purchase Agreement, sell this Warrant without
registration under the Securities Act within the limitation of the exemptions
provided by (A) Rule 144 under the Securities Act, as such rule may
be amended from time to time, or (B) any successor rule or regulation
hereafter adopted by the SEC. Upon the written request of any Warrantholder,
the Company will deliver to such Warrantholder a written statement that it has
complied with such requirements.

 

12.                                 Adjustments and Other Rights.
For so long as the Original Warrantholder holds this Warrant or any portion
thereof, if any event occurs that, in the good faith judgment of the Board of
Directors of the Company, would require adjustment of the Exercise Price or
number of Shares into which this Warrant is exercisable in order to fairly and
adequately protect the purchase rights of the Warrants in accordance with the
essential intent and principles of the Purchase Agreement and this Warrant,
then the Board of Directors shall make such adjustments in the application of
such provisions, in accordance with such essential intent and principles, as
shall be reasonably necessary, in the good faith opinion of the Board of
Directors, to protect such purchase rights as aforesaid.

 

Whenever the Exercise Price or the number of Shares
into which this Warrant is exercisable shall be adjusted as provided in this Section 12,
the Company shall forthwith file at the principal office of the Company a
statement showing in reasonable detail the facts requiring such adjustment and
the Exercise Price that shall be in effect and the number of Shares into which
this Warrant shall be exercisable after such adjustment, and the Company shall
also cause a copy of such statement to be sent by mail, first class postage
prepaid, to each Warrantholder at the address appearing in the Company’s
records.

 

13.                                 No Impairment. The
Company will not, by amendment of its Charter or through any reorganization,
transfer of assets, consolidation, merger, dissolution, issue or sale of
securities or any other voluntary action, avoid or seek to avoid the observance
or performance of any of the terms to be observed or performed hereunder by the
Company, but will at all times in good faith assist in the carrying out of all
the provisions of this Warrant and in taking of all such action as may be
necessary or appropriate in order to protect the rights of the Warrantholder.

 

14.                                 Governing Law. This
Warrant will be governed by and construed in accordance with the federal law of
the United States if and to the extent such law is applicable, and otherwise in
accordance with the laws of the State of New York applicable to contracts made
and to be performed entirely within such State. Each of the Company and the
Warrantholder agrees (a) to submit to the exclusive jurisdiction and venue
of the United States District Court for the District of Columbia for any civil
action, suit or proceeding arising out of or relating to this Warrant or the
transactions contemplated hereby, and (b) that notice may be served upon
the Company at the address in Section 17 below and upon the Warrantholder
at the address for the Warrantholder set forth in the registry maintained by
the Company pursuant to Section 8 hereof. 
To the extent permitted by applicable law, 

 

5

 

each of the Company and the Warrantholder hereby
unconditionally waives trial by jury in any civil legal action or proceeding
relating to the Warrant or the transactions contemplated hereby or thereby.

 

15.                                 Binding Effect. This
Warrant shall be binding upon any successors or assigns of the Company.

 

16.                                 Amendments. This
Warrant may be amended and the observance of any term of this Warrant may be
waived only with the written consent of the Company and the Warrantholder.

 

17.                                 Notices. Any
notice, request, instruction or other document to be given hereunder by any
party to the other will be in writing and will be deemed to have been duly
given (a) on the date of delivery if delivered personally, or by
facsimile, upon confirmation of receipt, or (b) on the second business day
following the date of dispatch if delivered by a recognized next day courier
service. All notices hereunder shall be delivered as set forth in Item 9 of
Schedule A hereto, or pursuant to such other instructions as may be designated
in writing by the party to receive such notice.

 

18.                                 Entire Agreement. This
Warrant, the forms attached hereto and Schedule A hereto (the terms of which
are incorporated by reference herein), and the Letter Agreement (including all
documents incorporated therein), contain the entire agreement between the
parties with respect to the subject matter hereof and supersede all prior and
contemporaneous arrangements or undertakings with respect thereto.

 

[Remainder
of page intentionally left blank]

 

6

 

[Form of Notice of Exercise]

	
   

  	
  Date:

  	
   

  	
   

  

 

TO:                            BankGreenville Financial
Corporation

 

RE:                              Election to Purchase
Preferred Stock

 

The undersigned, pursuant to the provisions
set forth in the attached Warrant, hereby agrees to subscribe for and purchase
the number of shares of the Preferred Stock set forth below covered by such
Warrant.  The undersigned, in accordance
with Section 3 of the Warrant, hereby agrees to pay the aggregate Exercise
Price for such shares of Preferred Stock in the manner set forth in Section 3(B) of
the Warrant.  A new warrant evidencing
the remaining shares of Preferred Stock covered by such Warrant, but not yet
subscribed for and purchased, if any, should be issued in the name set forth
below.

 

	
  Number of Shares of Preferred Stock

  	
   

  	
   

  
	
   

  	
   

  	
   

  
	
  Aggregate Exercise Price:

  	
   

  	
   

  

 

 

	
   

  	
  Holder:

  	
   

  
	
   

  	
  By:

  	
   

  
	
   

  	
  Name:

  	
   

  
	
   

  	
  Title:

  	
   

  

 

7

 

IN WITNESS WHEREOF, the Company has caused
this Warrant to be duly executed by a duly authorized officer.

 

	
  Dated: February 13,
  2009

  	
   

  	
   

  
	
   

  	
   

  	
   

  
	
   

  	
  BANKGREENVILLE FINANCIAL CORPORATION

  
	
   

  	
   

  
	
   

  	
  By:

  	
  /s/ Russel T. Williams

  
	
   

  	
  Name:

  	
  Russel T. Williams

  
	
   

  	
  Title:  Chief Executive Officer

  
	
   

  	
   

  	
   

  
	
   

  	
   

  	
   

  
	
   

  	
  Attest:

  
	
   

  	
   

  	
   

  
	
   

  	
   

  	
   

  
	
   

  	
  By:

  	
  /s/ Paula S. King

  
	
   

  	
  Name:

  	
  Paula S. King

  
	
   

  	
  Title:  Chief Financial Officer

  
						

 

 

[Signature Page to
Warrant]

 

8

 

SCHEDULE A

 

Item 1 

Name:  BankGreenville Financial
Corporation

Corporate or other organizational form: 
Corporation

Jurisdiction of organization:  South
Carolina

 

Item 2

 

Exercise Price: 
$.01

 

Item 3

Issue Date:  February 13,
2009

 

Item 4

Liquidation Amount: 
$1,000

 

Item 5

Series of Perpetual Preferred Stock:      Fixed Rate Cumulative
Perpetual Preferred Stock, Series B

 

Item 6

Date of Letter Agreement
between the Company and the United States Department of the Treasury:  February 13, 2009

 

Item 7

Number of shares of
Preferred Stock:  50.00050

 

	
  Item
  8

  	
   

  	
   

  
	
  Company’s
  address:

  	
  499
  Woodruff Road

  	
   

  
	
   

  	
  Greenville,
  South Carolina 29607

  	
   

  
	
   

  	
   

  	
   

  
	
  Item
  9

  	
   

  	
   

  
	
  Notice
  information:

  	
  Russel
  T. Williams

  	
   

  
	
   

  	
  Chief
  Executive Officer

  	
   

  
	
   

  	
  499 Woodruff Road

  	
   

  
	
   

  	
  Greenville, South Carolina 29607

  	
   

  
	
   

  	
   

  	
   

  
	
   

  	
  With a copy to:

  	
   

  
	
   

  	
   

  	
   

  
	
   

  	
  Benjamin A. Barnhill

  	
   

  
	
   

  	
  Nelson Mullins Riley & Scarborough
  LLP

  	
   

  
	
   

  	
  Suite 900, Poinsett Plaza

  	
   

  
	
   

  	
  104 S. Main Street

  	
   

  
	
   

  	
  Greenville, South Carolina 29601

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