(2S,3S,4S,5R,6S)-6-{[(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-6,12-dien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 169622
• Molecular Formular: C27H34O8
• Molecular Mass: 486.55406
• Monoisotopic Mass: 486.22536805
• SMILES: C1CC(=O)C=C2[C@H]1[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1)(CC)[C@@](C=C2)(C#C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1C=C[C@]2(C#C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CCC1=CC(=O)CC[C@H]31
• InChI: InChI=1S/C27H34O8/c1-3-26-11-9-17-16-8-6-15(28)13-14(16)5-7-18(17)19(26)10-12-27(26,4-2)35-25-22(31)20(29)21(30)23(34-25)24(32)33/h2,10,12-13,16-23,25,29-31H,3,5-9,11H2,1H3,(H,32,33)/t16-,17+,18+,19-,20-,21-,22+,23-,25-,26-,27-/m0/s1
• InChIKey: HRFIGUNIDWUIBL-HBRQQDTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,12-dien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,12-dien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (17α)-13-Ethyl-17-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one β-D-Glucuronide; Gestodene β-D-Glucuronide

Database IDs

• PubChem SID: 162263754
• PubChem CID: 71317067

CALCULATED PROPERTIES

• Acid pKa: 3.575386
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.0861274
• LogD (pH = 7.4): -1.3462565
• Log P: 2.0052214
• Molar Refractivity: 125.2688 cm^3
• Polarizability: 49.16023 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G368260

Gestodene β-D-Glucuronide is a metabolite of Gestodene (G368250).