(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,2S,7S,10R,11S,14S,15S)-14-(2H3)methyl-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-4-en-14-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 172470
• Molecular Formular: C26H40O7
• Molecular Mass: 464.5916
• Monoisotopic Mass: 464.27740362
• SMILES: C1=CC[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)C)C)C
• Canonical SMILES: OC(=O)[C@H]1O[C@@H](O[C@@]2(C)CC[C@@H]3[C@]2(C)CC[C@H]2[C@H]3CC[C@@H]3[C@]2(C)CC=CC3)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C26H40O7/c1-24-11-5-4-6-14(24)7-8-15-16(24)9-12-25(2)17(15)10-13-26(25,3)33-23-20(29)18(27)19(28)21(32-23)22(30)31/h4-5,14-21,23,27-29H,6-13H2,1-3H3,(H,30,31)/t14-,15-,16+,17+,18+,19+,20-,21+,23+,24+,25+,26+/m1/s1
• InChIKey: FCHSKWBEMZXALU-XKJUWYDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,2S,7S,10R,11S,14S,15S)-14-(^2H₃)methyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-4-en-14-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,2S,7S,10R,11S,14S,15S)-14-(^2H₃)methyl-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-4-en-14-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (5α,17β)-17-(Μethyl-d3)androst-2-en-17-ol; 17-(Methyl-d3)-5α-androst-2-en-17β-ol β-D-Glucopyranosiduronic Acid; Madol-d3 β-D-Glucuronide

Database IDs

• PubChem SID: 164228380
• PubChem CID: 71749871

CALCULATED PROPERTIES

• Acid pKa: 3.6846104
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.2448952
• LogD (pH = 7.4): -0.25304538
• Log P: 3.0585692
• Molar Refractivity: 120.9972 cm^3
• Polarizability: 48.54462 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M108012

A labelled metabolite of Madol.