(2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 170512
• Molecular Formular: C26H34O8
• Molecular Mass: 474.54336
• Monoisotopic Mass: 474.22536805
• SMILES: C1=CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2=C)[C@H]2[C@](CC1)([C@H](CC2)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)C(=C)C[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C)C
• InChI: InChI=1S/C26H34O8/c1-12-10-14-15-4-5-18(33-24-21(30)19(28)20(29)22(34-24)23(31)32)26(15,3)9-7-16(14)25(2)8-6-13(27)11-17(12)25/h6,8,11,14-16,18-22,24,28-30H,1,4-5,7,9-10H2,2-3H3,(H,31,32)/t14-,15-,16-,18-,19-,20-,21+,22-,24+,25+,26-/m0/s1
• InChIKey: XCZFLDRSNZFAQL-VPHACUKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-8-methylidene-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (17β)-6-Methylene-3-oxoandrosta-1,4-dien-17-yl β-D-Glucopyranosiduronic Acid, Methylene Boldenone Glucuronide; 17β-Hydroxy Exemestane 17-O-β-D-Glucuronide

Database IDs

• PubChem SID: 164226422
• PubChem CID: 71749003

CALCULATED PROPERTIES

• Acid pKa: 3.6274605
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.01680149
• LogD (pH = 7.4): -1.4812062
• Log P: 1.852059
• Molar Refractivity: 122.1299 cm^3
• Polarizability: 48.165863 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942350

17β-Hydroxy Exemestane 17-O-β-D-Glucuronide is the glucuronidated conjugate of the hydroxy metabolite of Exemestane (E957000).

REFERENCES

• Sun, D. et al.: Pharmacogen. Genom., 20, 575 (2010)