(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7S,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyl-17-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}oxane-2-carboxylic acid

• ChemBase ID: 159735
• Molecular Formular: C27H40O10
• Molecular Mass: 524.6005
• Monoisotopic Mass: 524.26214748
• SMILES: C1[C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=O)([C@H](CC2)C(=O)CO)C)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OCC(=O)[C@H]1CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@H](C2)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C27H40O10/c1-26-8-7-13(36-25-22(33)20(31)21(32)23(37-25)24(34)35)9-12(26)3-4-14-15-5-6-16(18(30)11-28)27(15,2)10-17(29)19(14)26/h12-16,19-23,25,28,31-33H,3-11H2,1-2H3,(H,34,35)/t12-,13+,14-,15-,16+,19+,20-,21-,22+,23-,25+,26-,27-/m0/s1
• InChIKey: MEVAPGVTSKDONA-IULWRGGCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7S,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyl-17-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7S,10S,11S,14S,15S)-14-(2-hydroxyacetyl)-2,15-dimethyl-17-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
• Synonyms: (3α,5α)-21-Hydroxy-11,20-dioxopregnan-3-yl β-D-Glucopyranosiduronic Αcid; Alphadolone 3-β-D-Glucuronide

Database IDs

• CAS Number: 70522-56-4
• PubChem SID: 162253870
• PubChem CID: 71313114

CALCULATED PROPERTIES

• Acid pKa: 3.4672441
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -1.2272645
• LogD (pH = 7.4): -2.58904
• Log P: 0.79587823
• Molar Refractivity: 127.5569 cm^3
• Polarizability: 51.538116 Å^3
• Polar Surface Area: 170.82 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A575515

Alphadolone 3-β-D-Glucuronide is a metabolite of Alphadolone (A575510).

REFERENCES

• Carlson, G.L., et al.: J. Steroid Biochem., 10, 161 (1979)