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

• ChemBase ID: 160643
• Molecular Formular: C25H38O8
• Molecular Mass: 466.56442
• Monoisotopic Mass: 466.25666818
• SMILES: C1C(=O)C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[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=C1CC[C@]2([C@H](C1)CC[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/C25H38O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h12,14-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1
• InChIKey: CLQMBSSRTBUNDV-CPKOJWPQSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 42037-24-1
• PubChem SID: 162254778
• PubChem CID: 44263365

CALCULATED PROPERTIES

• Acid pKa: 3.6274605
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.09183607
• LogD (pH = 7.4): -1.3725686
• Log P: 1.9606966
• Molar Refractivity: 115.8838 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 - A637655

Androstanolone 17-O-β-D-Glucuronide is the glucuronide conjugate of Androstanolone (A637540) and a major converion product of Testosterone (T155000). Studies show that Androstanolone 17-O-β-D-Glucuronide was significant lower in patients with benign prost

REFERENCES

• Moghissi, E. et al.: J. Clin. Endocrinol. Metab., 59, 417 (1984)
• Choi, M.H. et al.: Clin. Chem., 49, 322 (1984)