(2S,3S,4S,5R,6R)-6-{[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.02,7.011,15]heptadeca-7,13-dien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 158813
• Molecular Formular: C30H39NO7
• Molecular Mass: 525.63316
• Monoisotopic Mass: 525.27265259
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC=C1c1cccnc1)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@H]4CC=C3c3cccnc3)C)C2)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C30H39NO7/c1-29-11-9-18(37-28-25(34)23(32)24(33)26(38-28)27(35)36)14-17(29)5-6-19-21-8-7-20(16-4-3-13-31-15-16)30(21,2)12-10-22(19)29/h3-5,7,13,15,18-19,21-26,28,32-34H,6,8-12,14H2,1-2H3,(H,35,36)/t18-,19-,21-,22-,23-,24-,25+,26-,28+,29-,30+/m0/s1
• InChIKey: KPALNZWCXXEGPL-IZCNWNRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-(pyridin-3-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (3β)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol β-D-Glucuronide; Abiraterone β-D-Glucuronide

Database IDs

• PubChem SID: 162252948
• PubChem CID: 71312698

CALCULATED PROPERTIES

• Acid pKa: 3.4144793
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.7624845
• LogD (pH = 7.4): -0.7382449
• Log P: 1.4652241
• Molar Refractivity: 139.5831 cm^3
• Polarizability: 55.210274 Å^3
• Polar Surface Area: 129.34 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A108495

Abiraterone β-D-Glucuronide is a metabolite of Abiraterone (A108490).