JAZL/ChemGist-CHON huggingface dataset:
Compound: ISOBUTYL FORMATE
SMILES: O=COCC(C)C
InChIKey: AVMSWPWPYJVYKY-UHFFFAOYSA-N
Synonyms: ISOBUTYL FORMATE, 2-Methylpropyl formate, Formic acid, 2-methylpropyl ester, Tetryl formate, Isobutyl formate (natural), FEMA No. 2197, NSC 6968, UNII-6OCL1KXH0Q, 6OCL1KXH0Q, EINECS 208-818-1, UN2393, BRN 1738888, AI3-24240, Isobutyl formate, 8CI, NSC-6968, 2-Methylpropyl formate, 9CI, ISOBUTYL FORMATE [MI], ISOBUTYL FORMATE [FCC], ISOBUTYL FORMATE [FHFI], DTXSID7060257, FEMA 2197, 4-02-00-00029 (Beilstein Handbook Reference), UN 2393, 2Methylpropyl formate, 2Methyl1propyl formate, RefChem:149083, 2-Methylpropyl formic acid, DTXCID1041631, Formic acid, 2methylpropyl ester, 208-818-1, AVMSWPWPYJVYKY-UHFFFAOYSA-N, InChI=1/C5H10O2/c1-5(2)3-7-4-6/h4-5H,3H2,1-2H, 542-55-2, Isobutyl methanoate, Formic acid, isobutyl ester, Iso-butyl formate, 2-Methyl-1-propyl formate, Isobutyl methanote, Isobutylester kyseliny mravenci, Formic Acid Isobutyl Ester, MFCD00003293, Formic acid,2-methylpropyl ester, Isobutylester kyseliny mravenci [Czech], 2-methylpropyl ormate, Isobutyl formate, 97%, Isobutyl formate [UN2393] [Flammable liquid], SCHEMBL25811, SCHEMBL25812, WLN: VHO1Y1&1, SCHEMBL6807975, SCHEMBL11098606, SCHEMBL18812979, Isobutyl formate, >=95%, FG, NSC6968, CHEBI:173348, SBB061244, AKOS015903490, MSK167413-1000M, AS-87370, DB-052524, F0055, NS00012676, ST51047284, Isobutyl formate [UN2393]  [Flammable liquid], Isobutyl formate Solution in Methanol, 1000ug/mL, Q6085377
Theoretical properties:
molecular_formula: C5H10O2
molecular_weight: 102.13 g/mol
exact_mass: 102.068079557 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 7
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 97.00 to 99.00 °C. @ 760.00 mm Hg
melting_point: -95 °C
density: 0.876-0.886
solubility: 10.2 mg/mL at 25 °C
flash_point: less than 70 °F (NFPA, 2010)
vapor_pressure: 40.1 [mmHg]
Descriptions:
pubchem: 2-Methylpropyl formate is a carboxylic ester.
wikipedia: Isobutyl formate (2-methylpropyl methanoate) is an organic ester with the chemical formula C5H10O2. It is formed by the Fischer esterification of isobutanol with formic acid, with the aid of an acid catalyst. It is used as a flavor and fragrance ingredient because of its odor which is sweet, ethereal, and slightly fruity.
Compound: heptan-3-ol
SMILES: OC(CCCC)CC
InChIKey: RZKSECIXORKHQS-UHFFFAOYSA-N
Synonyms: heptan-3-ol, 3-HEPTANOL, 589-82-2, 3-Hydroxyheptane, Butyl ethyl carbinol, Ethyl butyl carbinol, FEMA No. 3547, DL-3-Heptanol, NSC 2586, 1-Ethyl-1-pentanol, EINECS 209-661-1, 12YBT48HMK, BRN 1719067, AI3-21994, NSC-2586, 3-HEPTANOL [FHFI], DTXSID50862251, 4-01-00-01741 (Beilstein Handbook Reference), 3Hydroxyheptane, nButyl ethyl carbinol, RefChem:502126, DTXCID30811045, 209-661-1, BUTYLETHYLCARBINOL, (+/-)-3-Heptanol, (R)-heptan-3-ol, xi-3-Heptanol, MFCD00004586, 62701-49-9, UNII-12YBT48HMK, Ethylbutylcarbinol, heptanol-3, 3-Heptyl Alcohol, n-Heptan-3-ol, Ethyl-n-butylcarbinol, 3-Heptanol, 99%, 3-Heptanol, >=98%, SCHEMBL26280, SCHEMBL290688, SCHEMBL497218, CHEMBL452729, SCHEMBL1665106, SCHEMBL1665110, SCHEMBL1871154, SCHEMBL6085514, SCHEMBL8561119, WLN: QY4&2, 3-Heptanol, analytical standard, CH3(CH2)3CHOHCH2CH3, SCHEMBL10433133, SCHEMBL18280923, NSC2586, CHEBI:179170, 3-HEPTANOL, (+/-)-, NSC88870, LMFA05000483, NSC-88870, AKOS009156766, EBC-627158, AS-81603, CS-0137777, H0035, NS00012516, E78220, EN300-6504531, F240666, Q4634146, InChI=1/C7H16O/c1-3-5-6-7(8)4-2/h7-8H,3-6H2,1-2H, 40617-58-1
Theoretical properties:
molecular_formula: C7H16O
molecular_weight: 116.20 g/mol
exact_mass: 116.120115130 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 4
heavy_atom_count: 8
topological_polar_surface_area: 20.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
density: 0.815-0.821
solubility: insoluble in water; soluble in alcohol
vapor_pressure: 0.74 [mmHg]
Descriptions:
pubchem: Heptan-3-ol is a secondary alcohol that is heptane substituted by a hydroxy group at position 3. It has a role as a plant metabolite. It is a heptanol and a secondary alcohol.
chebi: A secondary alcohol that is heptane substituted by a hydroxy group at position 3.
chembl: 3-HEPTANOL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: 3-Heptanol or heptan-3-ol is an organic alcohol with the chemical formula C7H16O.
3-Heptanol is chiral, so (R)- and (S)- isomers exist.
Compound: 4-Heptanone
SMILES: O=C(CCC)CCC
InChIKey: HCFAJYNVAYBARA-UHFFFAOYSA-N
Synonyms: 4-Heptanone, Heptan-4-one, 123-19-3, Dipropyl ketone, Butyrone, Propyl ketone, Di-n-propyl ketone, 4-Oxoheptane, FEMA No. 2546, 9BN582JQ61, NSC-8692, DTXSID6047650, CHEBI:89484, RefChem:99080, DTXCID4027650, 204-608-9, NSC 8692, MFCD00009403, 4-Heptanone (natural), EINECS 204-608-9, UN2710, BRN 1699049, dipropylketon, dipropylketone, UNII-9BN582JQ61, AI3-15181, HSDB 7908, heptane-4-one, 4-Heptanone, 98%, 4-HEPTANONE [FHFI], SCHEMBL25174, DIPROPYL KETONE [MI], 4-01-00-03323 (Beilstein Handbook Reference), SCHEMBL127466, SCHEMBL128191, (n-C3H7)2CO, SCHEMBL6932133, WLN: 3V3, 4-Heptanone, >=97%, FG, SCHEMBL25403152, 4-Heptanone, analytical standard, NSC8692, BBL009715, LMFA12000118, SBB060386, STL141080, AKOS000118993, EBC-627115, MSK164731-100B, UN 2710, BP-12815, VS-02154, 4-Heptanone Solution in Acetone, 100ug/mL, H0039, NS00012348, ST51046576, EN300-19142, Dipropyl ketone [UN2710]  [Flammable liquid], Q1287920, InChI=1/C7H14O/c1-3-5-7(8)6-4-2/h3-6H2,1-2H
Theoretical properties:
molecular_formula: C7H14O
molecular_weight: 114.19 g/mol
exact_mass: 114.104465066 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 1
rotatable_bond_count: 4
heavy_atom_count: 8
topological_polar_surface_area: 17.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Stable, colorless liquid
color: Stable, colorless liquid
odor: Pleasant odor
boiling_point: 291 °F at 760 mmHg (NIOSH, 2024)
melting_point: -27 °F (NIOSH, 2024)
density: 0.82 (NIOSH, 2024) - Less dense than water; will float
solubility: Insoluble (NIOSH, 2024)
flash_point: 120 °F (NIOSH, 2024)
vapor_pressure: 5 mmHg (NIOSH, 2024)
Descriptions:
pubchem: 4-heptanone is a dialkyl ketone that is heptane in which the two methylene protons at position 4 have been replaced by an oxo group. It has a role as a biomarker, a human xenobiotic metabolite, a human urinary metabolite and a rat metabolite. It derives from a hydride of a heptane.
chebi: A dialkyl ketone that is heptane in which the two methylene protons at position 4 have been replaced by an oxo group.
wikipedia: 4-Heptanone or heptan-4-one is an organic compound with the formula (CH3CH2CH2)2CO. It is a colorless liquid.
Compound: Acetic oxalic anhydride
SMILES: O=C(OC(=O)C)C(=O)OC(=O)C
InChIKey: XRMBFFGBVGXJJF-UHFFFAOYSA-N
Synonyms: Acetic oxalic anhydride, Diacetyloxalate, B7JR77WDN2, 19037-85-5, UNII-B7JR77WDN2, Acetic acid, dianhydride with oxalic acid, Oxalic acid, dianhydride with acetic acid, Ethanedioic acid, 1,2-dianhydride with acetic acid, acetoxy diketone, SCHEMBL3177567, DTXSID20711666, Q4673257
Theoretical properties:
molecular_formula: C6H6O6
molecular_weight: 174.11 g/mol
exact_mass: 174.01643791 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 5
heavy_atom_count: 12
topological_polar_surface_area: 86.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: Acetic oxalic anhydride is an organic compound with a chemical formula of C6H6O6 and a structural formula of (H3C-(C=O)-O-(C=O)-)2.  It can be viewed as a mixed anhydride, formally derived from acetic acid (H3C-(C=O)OH) and oxalic acid ((-(C=O)OH)2), in 2:1 molecular ratio, by the loss of two water molecules.
Compound: Formyl acetate
SMILES: O=C(OC=O)C
InChIKey: ORWKVZNEPHTCQE-UHFFFAOYSA-N
Synonyms: Formyl acetate, 2258-42-6, Acetic acid, anhydride with formic acid, acetic-formic anhydride, GNF4F3WBU5, DTXSID80177103, RefChem:1075861, DTXCID8099594, Acetic formic anhydride, Formic acetic anhydride, acetyl formate, o-formyl acetate, formic-acetic anhydride, O-Formyl Acetate  (Technical Grade), Acetyl formyl anhydride, UNII-GNF4F3WBU5, formic acidacetic anhydride, formic acid-acetic anhydride, formic-acetic acid anhydride, SCHEMBL135686, SCHEMBL384596, SCHEMBL717371, SCHEMBL6881532, CAA25842, MFCD13184316, AKOS025117526, DA-21245, NS00124161, Q4673256
Theoretical properties:
molecular_formula: C3H4O3
molecular_weight: 88.06 g/mol
exact_mass: 88.016043985 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 6
topological_polar_surface_area: 43.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: Acetic formic anhydride is an organic compound with the chemical formula  C3H4O3, which can be viewed as the mixed anhydride of acetic acid and formic acid. It is used on a laboratory-scale as a formylating agent.
Compound: cis-Whiskey lactone
SMILES: O=C1O[C@H](CCCC)[C@@H](C1)C
InChIKey: WNVCMFHPRIBNCW-HTQZYQBOSA-N
Synonyms: cis-Whiskey lactone, cis-Oaklactone, cis-Methyloctanolide, 55013-32-6, Whiskey lactone, (Z)-, FEMA No. 3803, Z-, (+-)-cis-Whiskey lactone, beta-Methyl-gamma-octalactone, cis-, O93PZ85MTG, 5-Butyl-4-methyldihydro-2(3H)-furanone, (Z)-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, cis-, cis-beta-Methyl-gamma-Octalactone, 5-Butyl-4-methyldihydrofuran-2(3H)-one, (Z)-, cis-.beta.-Methyl-.gamma.-Octalactone, 5-BUTYLDIHYDRO-4-METHYL-2(3H)-FURANONE (CIS), 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5R)-rel-, RefChem:439873, cis-3-Methyl-4-octanolide, (4R,5R)-5-butyl-4-methyloxolan-2-one, (Z)-Oak lactone, (+/-)-cis-Whiskey lactone, 105015-53-0, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5R)-, (+)-CIS-WHISKEY LACTONE, 9678LTP737, (4R,5R)-5-BUTYLDIHYDRO-4-METHYL-2(3H)-FURANONE, (Z)-Oaklactone, (cis)-Oak-lactone, UNII-O93PZ85MTG, (.+/-.)-cis-Whiskey lactone, UNII-9678LTP737, cis-4-methyl-5-butyldihydro-2(3H)-furanone, cis-5-Butyl-4-methyldihydrofuran-2(3H)-one, FEMA No. 3803, cis-(+-)-, cis-3-Methyl-4-octanolid, 5-Butyl-4-methyldihydro-2(3H)-furanone, cis-(+-)-, SCHEMBL9171097, CHEBI:171765, DTXSID801009384, DB-247110, NS00126379, cis-(+)-5-Butyl-4-methyldihydro-2(3H)-furanone, Q5122105, (4R,5r)-rel-5-butyldihydro-4-methyl-2(3h)-furanone, 5-BUTYL-4-METHYLDIHYDRO-2(3H)-FURANONE, CIS-(+)-
Theoretical properties:
molecular_formula: C9H16O2
molecular_weight: 156.22 g/mol
exact_mass: 156.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 11
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (Z)-Oak lactone is a gamma-lactone.
wikipedia: cis-3-Methyl-4-octanolide, also called cis-β-methyl-γ-octalactone or 5-butyldihydro-4-methylfuran-2(3H)-one, is a chemical compound of the lactone family with formula C9H16O2.  It exists in two optical isomers: 3R,4R ("+") and 3S,4S ("−").
The 3S,4S isomer, commonly known as whisky lactone or quercus lactone is an important ingredient in the aroma of whiskey (where it was first identified by Suomalainen and Nykänen in 1970) and other alcoholic beverages that have been aged in oak barrels. It is sometimes added to the liquor as a flavoring agent. It has a coconut, celery or fresh wood aroma, that can be detected by humans at the concentration of 1 μg/L in air. A mixture of the cis and trans isomers is repellent for mosquitos and flies.
The 3S,4S isomer is extracted by the alcoholic beverage from some precursor substances in the oak wood.  It can be synthesized from a cyclopentane derivative.
Compound: Quercus lactone B
SMILES: O=C1O[C@@H](CCCC)[C@H](C1)C
InChIKey: WNVCMFHPRIBNCW-YUMQZZPRSA-N
Synonyms: Quercus lactone B, (-)-cis-Whiskey lactone, DR7KRE2AJV, UNII-DR7KRE2AJV, 5-Butyl-4-methyldihydro-2(3H)-furanone, cis-(-)-, 80041-00-5, FEMA No. 3803, cis-(-)-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4S,5S)-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4S-cis)-, DTXSID60230043, .BETA.-METHYL-.GAMMA.-OCTALACTONE, CIS-(3S,4S)-, RefChem:102229, DTXCID60152534, BETA-METHYL-GAMMA-OCTALACTONE, CIS-(3S,4S)-, (Z)-Oaklactone, (cis)-Oak-lactone, (.+/-.)-cis-Whiskey lactone, cis-4-methyl-5-butyldihydro-2(3H)-furanone, cis-5-Butyl-4-methyldihydrofuran-2(3H)-one, (4S,5S)-5-butyl-4-methyloxolan-2-one, (Z)-WHISKEY LACTONE, SCHEMBL9171420, WNVCMFHPRIBNCW-YUMQZZPRSA-N, (3s,4s)-3-methyl-4-octanolide, cis-(-)-5-butyl-4-methyldihydro-2(3H)-furanone, Q27276558, Cis-(4S,5S)-5-butyl-4-methyldihydrofuran-2(3H)-one
Theoretical properties:
molecular_formula: C9H16O2
molecular_weight: 156.22 g/mol
exact_mass: 156.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 11
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: Ellagic acid is a polyphenol found in numerous fruits and vegetables. It is the dilactone of hexahydroxydiphenic acid.
Compound: (-)-trans-Quercus lactone
SMILES: O=C1O[C@@H](CCCC)[C@@H](C1)C
InChIKey: WNVCMFHPRIBNCW-SFYZADRCSA-N
Synonyms: (-)-trans-Quercus lactone, (-)-trans-Whiskey lactone, (-)-trans-Whisky lactone, UNII-9OQS29SV9M, 9OQS29SV9M, FEMA No. 3803, trans-(-)-, 5-Butyl-4-methyldihydro-2(3H)-furanone, trans-(-)-, 105119-22-0, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5S)-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R-trans)-, t-Whiskylactone, (E)-Whiskylactone, trans-5-butyl-4-methyldihydrofuran-2(3h)-one, (4R,5S)-5-butyl-4-methyloxolan-2-one, SCHEMBL9172090, DTXSID20146959, WNVCMFHPRIBNCW-SFYZADRCSA-N, trans-Quercus lactone, analytical standard, Q7833482, trans-(-)-5-butyl-4-methyldihydro-2(3H)-furanone, Rel-(4R,5S)-5-butyl-4-methyldihydrofuran-2(3H)-one, trans-4-Hydroxy-3-methyloctanoic acid, .gamma.-lactone, .BETA.-METHYL-.GAMMA.-OCTALACTONE, TRANS-(3R,4S)-
Theoretical properties:
molecular_formula: C9H16O2
molecular_weight: 156.22 g/mol
exact_mass: 156.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 11
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: cis-3-Methyl-4-octanolide, also called cis-β-methyl-γ-octalactone or 5-butyldihydro-4-methylfuran-2(3H)-one, is a chemical compound of the lactone family with formula C9H16O2.  It exists in two optical isomers: 3R,4R ("+") and 3S,4S ("−").
The 3S,4S isomer, commonly known as whisky lactone or quercus lactone is an important ingredient in the aroma of whiskey (where it was first identified by Suomalainen and Nykänen in 1970) and other alcoholic beverages that have been aged in oak barrels. It is sometimes added to the liquor as a flavoring agent. It has a coconut, celery or fresh wood aroma, that can be detected by humans at the concentration of 1 μg/L in air. A mixture of the cis and trans isomers is repellent for mosquitos and flies.
The 3S,4S isomer is extracted by the alcoholic beverage from some precursor substances in the oak wood.  It can be synthesized from a cyclopentane derivative.
Compound: Trans-3-Methyl-4-octanolide
SMILES: O=C1O[C@H](CCCC)[C@H](C1)C
InChIKey: WNVCMFHPRIBNCW-JGVFFNPUSA-N
Synonyms: Trans-3-Methyl-4-octanolide, trans-Oaklactone, trans-Whiskey lactone, 39638-67-0, Whiskey lactone, (E)-, (+-)-trans-Whiskey lactone, FEMA No. 3803, trans-, 29IPH2W8KP, trans-beta-Methyl-gamma-octalactone, 5-Butyl-4-methyldihydro-2(3H)-furanone, trans-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, trans-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5S)-rel-, trans-4-Hydroxy-3-methyloctanoic acid gamma-lactone, TRANS-.BETA.-METHYL-.GAMMA.-OCTALACTONE, .BETA.-METHYL-.GAMMA.-OCTALACTONE, TRANS-, TRANS-4-HYDROXY-3-METHYLOCTANOIC ACID .GAMMA.-LACTONE, RefChem:534161, BETA-METHYL-GAMMA-OCTALACTONE, TRANS-, 110-387-9, Quercus lactone A, (3S,4R)-3-methyl-4-octanolide, (+/-)-trans-Whiskey lactone, (+-)-Quercus lactone, (+-)-Whiskey lactone, (+-)-trans-Whisky lactone, (+-)-trans-Quercus lactone, UNII-7A29T3GS95, (4S,5R)-5-butyl-4-methyloxolan-2-one, 7A29T3GS95, 80041-01-6, FEMA No. 3803, trans-(+-)-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4S,5R)-, 2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4S-trans)-, trans-5-butyl-4-methyldihydrofuran-2(3h)-one, UNII-29IPH2W8KP, (+)-TRANS-QUERCUS LACTONE, (E)-Whiskeylactone, trans-Wiskey lactone, (+)-QUERCUS LACTONE, (+)-WHISKEY LACTONE, SCHEMBL7178100, 5-Butyl-4-methyldihydro-2(3H)-furanone, trans-(+-)-, (+)-TRANS-WHISKY LACTONE, DTXSID801017484, (+)-TRANS-WHISKEY LACTONE, (3S, 4R)-3-methyl-4-octanolide, MFCD29904979, (E)-Oaklactone,(trans)-3-methyloctanoicacid-gamma-lactone,(+)-trans-whiskeylactone,5-butyldihydro-4-methyl-2(3H)-furanone, SY319380, FEMA NO. 3803, TRANS-(+)-, (trans)-3-methyloctanoic acid-gamma-lactone, .BETA.-METHYL-.GAMMA.-OCTALACTONE, TRANS-(3S,4R)-, 5-BUTYL-4-METHYLDIHYDRO-2(3H)-FURANONE, TRANS-(+)-
Theoretical properties:
molecular_formula: C9H16O2
molecular_weight: 156.22 g/mol
exact_mass: 156.115029749 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 3
heavy_atom_count: 11
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: trans-3-Methyl-4-octanolide, also called trans-β-methyl-γ-octalactone is a chemical compound of the lactone family with formula C9H16O2.  It exists in two stereoisomers: (3R,4S) and (3S,4R).
The (3S,4R) form is found in whiskey and other alcoholic beverages that have been aged in oak barrels, together with the more important cis isomer. It has a coconut, celery or fresh wood aroma, that can be detected by humans at the concentration of 20 μg/L in air.  A mixture of the cis and trans isomers is repellent for mosquitos and flies.
The (3S,4R) isomer is extracted by the alcoholic beverage from some precursor substances in the oak wood.  It can be synthesized in various ways.
Compound: trans-4-Hydroxy-3-methyldecanoic acid lactone
SMILES: O=C1O[C@@H](CCCCCC)[C@@H](C1)C
InChIKey: XNRLAEXLQFIKEY-ZJUUUORDSA-N
Synonyms: trans-4-Hydroxy-3-methyldecanoic acid lactone, SCHEMBL18086466, XNRLAEXLQFIKEY-ZJUUUORDSA-N, 5-Hexyl-4-methyldihydro-2(3H)-furanone, trans-
Theoretical properties:
molecular_formula: C11H20O2
molecular_weight: 184.27 g/mol
exact_mass: 184.146329876 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 5
heavy_atom_count: 13
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
Compound: FEMA No. 3999, trans-
SMILES: O=C1O[C@H](CCCCCC)[C@H](C1)C
InChIKey: XNRLAEXLQFIKEY-VHSXEESVSA-N
Synonyms: FEMA No. 3999, trans-, XN9I5FD92J, 2(3H)-Furanone, 5-hexyldihydro-4-methyl-, trans-, 3-Methyl-gamma-decalactone, trans-, 147254-33-9, 2(3H)-Furanone, 5-hexyldihydro-4-methyl-, (4R,5S)-rel-, RefChem:1097998, rel-(4R,5S)-5-Hexyldihydro-4-methyl-2(3H)-furanone, UNII-XN9I5FD92J, (+-)-3-Methyl-gamma-decalactone, trans-, SCHEMBL1793652, trans-3-methyl-gamma-decalactone, DTXSID001029637, 3-METHYL-.GAMMA.-DECALACTONE, TRANS-, (4S,5R)-5-Hexyl-4-methyldihydro-2(3H)-furanone, Q7833483, (+/-)-3-METHYL-.GAMMA.-DECALACTONE, TRANS-
Theoretical properties:
molecular_formula: C11H20O2
molecular_weight: 184.27 g/mol
exact_mass: 184.146329876 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 5
heavy_atom_count: 13
topological_polar_surface_area: 26.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
wikipedia: This is a list of episodes for The Daily Show, a late-night talk and satirical news television program airing on Comedy Central, during 2025 (the series' 30th season). Jon Stewart serves as host once each week (primarily on Mondays), while other members of the show's correspondence roster ("The Best F#@king News Team") rotate sitting in the anchor chair the rest of the week.
Compound: 1,4,8,11-Tetraazacyclotetradecane
SMILES: N1CCNCCCNCCNCCC1
InChIKey: MDAXKAUIABOHTD-UHFFFAOYSA-N
Synonyms: 1,4,8,11-Tetraazacyclotetradecane, 295-37-4, Cyclam, EP5AZ544VP, JM 1498, CHEBI:37401, NSC-180811, DTXSID30183698, NSC-80811, JM-1498, RefChem:129168, DTXCID70106189, 206-039-1, MFCD00005105, 1,4,8,11-tetrazacyclotetradecane, C10H24N4, [14]aneN4, CHEMBL125150, 1,4,8,11-tetraazacyclo-tetradecane, IPS2, EINECS 206-039-1, NSC 180811, BRN 0111811, Cyclam?, Plerixafor Impurity 7, 14-crown-4N4, Cyclam(1,4,8,11-Tetraazacyclotetradecane), UNII-EP5AZ544VP, SCHEMBL33477, CBDivE_013909, 5-26-11-00027 (Beilstein Handbook Reference), MLS000069469, SCHEMBL674050, orb1089619, orb3029457, SCHEMBL1779850, SCHEMBL1781243, SCHEMBL1781729, SCHEMBL1782168, SCHEMBL1783483, 1,8,11-Tetraazacyclotetradecane, PDK0168, 1,4,8,11-Tetraacyclotetradecane, 1,4,8,11Tetraaza-Cyclotetradecane, BDBM50615205, JM1498, NSC180811, SBB056222, STL333618, 1,4,8,11-tetraaza-cyclotetradecane, 1,4,8,11-tetra-aza cyclotetradecane, AKOS015854525, CS-W019774, EBC-381047, FC02708, NCGC00018136-01, NCGC00018136-02, NCGC00018136-03, AS-19218, SMR000059059, SY010380, DB-047596, NS00028722, ST45255341, T1597, EN300-202126, 1,4,8,11-Tetraazacyclotetradecane, 98% (GC), F151835, Q1970333, Z1269214154
Theoretical properties:
molecular_formula: C10H24N4
molecular_weight: 200.32 g/mol
exact_mass: 200.20009678 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 0
heavy_atom_count: 14
topological_polar_surface_area: 48.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: 1,4,8,11-tetraazacyclotetradecane is a saturated organic heteromonocyclic parent, a crown amine and an azacycloalkane. It derives from a hydride of a cyclotetradecane.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Plerixafor, sold under the brand name Mozobil, is an immunostimulant used to mobilize hematopoietic stem cells in cancer patients into the bloodstream. The stem cells are then extracted from the blood and transplanted back to the patient. The drug was developed by AnorMED, which was subsequently bought by Genzyme.
SMILES: [C@@]12([C@H]([C@]3(C([C@@H]([C@@H](CCCC(C)C)C)CC3)(C)CC1)C)CC[C@@H]4[C@H]2CCCC4(C)C)C
InChIKey: ZYZJWAJOTPNVPI-NXJMPBGFSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: A triterpene that is an isomer of lanostane obtained by migration of the methyl group from 10 to the 9β position.
SMILES: [C@@]12([C@H]([C@]3(C([C@@H]([C@@H](CCCC(C)C)C)CC3)(C)CC1)C)CC[C@H]4[C@H]2CCCC4(C)C)C
InChIKey: ZYZJWAJOTPNVPI-AVANRTMUSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: A triterpene that is an isomer of lanostane obtained by migration of the methyl group from 10 to the 9β position.
SMILES: [C@]12([C@H](C(CCC1)(C)C)CC[C@@H]3[C@H]2CCC4([C@]3(CC[C@@H]4[C@@H](CCCC(C)C)C)C)C)C
InChIKey: ZQIOPEXWVBIZAV-AFRFLVTJSA-N
Theoretical properties:
Physical properties:
Descriptions:
SMILES: [C@]12([C@@H](C(CCC1)(C)C)CC[C@@H]3[C@H]2CCC4([C@]3(CC[C@@H]4[C@@H](CCCC(C)C)C)C)C)C
InChIKey: ZQIOPEXWVBIZAV-HQFDYZEFSA-N
Theoretical properties:
Physical properties:
Descriptions:
SMILES: O=C(O[C@H]1[C@H](O[C@@H]2O[C@H]([C@H](O)[C@H]([C@H]2O)O)C)[C@@H](O)[C@H](OCCc3cc(O)c(O)cc3)O[C@@H]1CO)/C=C/c4cc(O)c(O)cc4
InChIKey: FBSKJMQYURKNSU-ZLSOWSIRSA-N
Theoretical properties:
Physical properties:
Descriptions:
chebi: A glycoside that is the α-<small>L</small>-rhamnosyl-(1→3)-β-<small>D</small>-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with <i>trans</i>-caffeic acid.
chembl: ACETOSIDE is a oligosaccharide listed in the ChEMBL database and has reached clinical trial phase 2.0.