(2S,3S,4S,5R,6R)-6-{[(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-(2H3)methyl(6,7,7,7-2H4)heptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 179542
• Molecular Formular: C33H52O7
• Molecular Mass: 560.76178
• Monoisotopic Mass: 560.371304
• SMILES: C1[C@H](CCC(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](CCCC(C)C)C)C)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C/1\C[C@H](CCC1=C)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C)C
• InChI: InChI=1S/C33H52O7/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-33(25,26)5)12-13-23-18-24(14-11-20(23)3)39-32-29(36)27(34)28(35)30(40-32)31(37)38/h12-13,19,21,24-30,32,34-36H,3,6-11,14-18H2,1-2,4-5H3,(H,37,38)/b22-12+,23-13-/t21-,24+,25-,26+,27+,28+,29-,30+,32-,33-/m1/s1
• InChIKey: HSMHKPFJPOTDCW-MFDWXRHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{[(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-(^2H₃)methyl(6,7,7,7-^2H₄)heptan-2-yl]-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{[(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-7a-methyl-1-[(2R)-6-(^2H₃)methyl(6,7,7,7-^2H₄)heptan-2-yl]-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-yl-d7 β-D-Glucopyranosiduronic Acid; Cholecalciferol-d7 Glucuronide; Vitamin D3 β-D-Glucuronide-d7

Database IDs

• PubChem SID: 164235452
• PubChem CID: 71752976

CALCULATED PROPERTIES

• Acid pKa: 3.5609818
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 3.7419229
• LogD (pH = 7.4): 2.3186324
• Log P: 5.6748996
• Molar Refractivity: 155.5052 cm^3
• Polarizability: 61.630653 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - V676052

A labelled metabolite of Vitamin D3.

REFERENCES

• Bell, P.A., et al.: Biochem. J., et al.: 115, 663 (1969)
• Kumar, R.S., et al.: J. Clin. Invest., 65, 277 (1969)
• Shimada, K., et al.: Biol. Pharm. Bull., 19, 491 (1969)