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

• ChemBase ID: 168032
• Molecular Formular: C25H38O8
• Molecular Mass: 466.56442
• Monoisotopic Mass: 466.25666818
• SMILES: C1[C@@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1O[C@@H](O[C@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2CCC3=O)C)C)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13-,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1
• InChIKey: VFUIRAVTUVCQTF-PALHZPRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1S,2S,5S,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1S,2S,5S,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (3β,5α)-17-Oxoandrostan-3-yl β-D-Glucopyranosiduronic Acid; 17-Oxo-5α-androstan-3β-yl β-D-Glucopyranosiduronic Acid; 17-Oxo-5α-androstan-3β-yl β-D-Glucosiduronic Acid; Epiandrosterone Glucuronide; 3β-(β-D-Glucopyranurononosyloxy)-5α-androstan-17-one; Epiandrosterone β-D-Glucuronide

Database IDs

• CAS Number: 4271-00-5
• PubChem SID: 162262164
• PubChem CID: 10298641

CALCULATED PROPERTIES

• Acid pKa: 3.4672441
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.2935807
• LogD (pH = 7.4): -1.0681946
• Log P: 2.3167233
• Molar Refractivity: 116.0896 cm^3
• Polarizability: 47.0811 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E578010

A C19-steroid metabolite of the androgen Epi Andesterone (E578000).

REFERENCES

• Martin, F. et al.: J. Steroid Biochem., 8, 753 (1977)
• Yamamoto, Y. et al.: Gen. Pharmacol., 21, 435 (1977)