(2S,3S,4S,5R,6S)-6-{[(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidene-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 168818
• Molecular Formular: C28H36O8
• Molecular Mass: 500.58064
• Monoisotopic Mass: 500.24101811
• SMILES: C1CC(=O)C=C2[C@H]1[C@@H]1[C@@H](CC2)[C@H]2[C@@](CC1=C)(CC)[C@@](CC2)(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)[C@H]3[C@H]([C@@H]1CC[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/C28H36O8/c1-4-27-13-14(3)20-17-9-7-16(29)12-15(17)6-8-18(20)19(27)10-11-28(27,5-2)36-26-23(32)21(30)22(31)24(35-26)25(33)34/h2,12,17-24,26,30-32H,3-4,6-11,13H2,1H3,(H,33,34)/t17-,18-,19-,20+,21-,22-,23+,24-,26-,27-,28-/m0/s1
• InChIKey: ZEIPQROXKPESNS-UYWVDHFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-17-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Etonogestrel β-D-Glucuronide

Database IDs

• PubChem SID: 162262950
• PubChem CID: 71316693

CALCULATED PROPERTIES

• Acid pKa: 3.5515032
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.20850003
• LogD (pH = 7.4): -1.2087529
• Log P: 2.1506088
• Molar Refractivity: 128.6323 cm^3
• Polarizability: 50.99108 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E933630

A metabolite of Etonogestrel.