(2S,3S,4S,5R,6R)-6-{[(1S,3Z,5R)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-5-hydroxy-2-methylidenecyclohexyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 167900
• Molecular Formular: C34H52O9
• Molecular Mass: 604.77128
• Monoisotopic Mass: 604.36113324
• SMILES: C1[C@H](C[C@@H](C(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](/C=C/[C@@H](C(O)(C)C)C)C)C)O[C@H]1[C@@H]([C@@H]([C@@H]([C@H](O1)C(=O)O)O)O)O)O
• Canonical SMILES: O[C@H]1C[C@H](O[C@@H]2O[C@H](C(=O)O)[C@H]([C@H]([C@H]2O)O)O)C(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](C(O)(C)C)C)C)C)/C1
• InChI: InChI=1S/C34H52O9/c1-18(9-10-19(2)33(4,5)41)24-13-14-25-21(8-7-15-34(24,25)6)11-12-22-16-23(35)17-26(20(22)3)42-32-29(38)27(36)28(37)30(43-32)31(39)40/h9-12,18-19,23-30,32,35-38,41H,3,7-8,13-17H2,1-2,4-6H3,(H,39,40)/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,27+,28+,29-,30+,32-,34-/m1/s1
• InChIKey: YFTAAIVSIYJCCN-SMMRVWHDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1S,3Z,5R)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-5-hydroxy-2-methylidenecyclohexyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1S,3Z,5R)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-5-hydroxy-2-methylidenecyclohexyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (1α,3β,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-1,3,25-triol 1α-O-β-D-Glucuronide; 1,25-Dihydroxycalciferol 1α-O-β-D-Glucuronide; 1,25-Dihydroxyergocalciferol; Ercalcitriol 1α-O-β-D-Glucuronide; Ro 17-6218 1α-O-β-D-Glucuronide; 1α,25-Dihydroxy Vitamin D2 1α-O-β-D-Glucuronide

Database IDs

• PubChem SID: 162262033
• PubChem CID: 71316281

CALCULATED PROPERTIES

• Acid pKa: 3.5744095
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): 0.98318535
• LogD (pH = 7.4): -0.4485784
• Log P: 2.9032311
• Molar Refractivity: 164.4014 cm^3
• Polarizability: 64.50087 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D455100

A metabolite of 1α,25-Dihydroxy Vitamin D2 (D455065).

REFERENCES

• Lam, H., et al.: Science, 186, 1038 (1974)
• Dilworth, F., et al.: J. Biol. Chem., 270, 16766 (1974)