(1R,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-(2H3)methyl(7,7,7-2H3)heptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

• ChemBase ID: 171453
• Molecular Formular: C27H44O2
• Molecular Mass: 400.63706
• Monoisotopic Mass: 400.33413065
• SMILES: C1[C@@H](CCC(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](CCCC(O)(C)C)C)C)O
• Canonical SMILES: O[C@@H]1CCC(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CCCC(O)(C)C)C)C)/C1
• InChI: InChI=1S/C27H44O2/c1-19-10-13-23(28)18-22(19)12-11-21-9-7-17-27(5)24(14-15-25(21)27)20(2)8-6-16-26(3,4)29/h11-12,20,23-25,28-29H,1,6-10,13-18H2,2-5H3/b21-11+,22-12-/t20-,23-,24-,25+,27-/m1/s1
• InChIKey: JWUBBDSIWDLEOM-UEGFJKGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-(^2H₃)methyl(7,7,7-^2H₃)heptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• IUPAC Traditional name: (1R,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-(^2H₃)methyl(7,7,7-^2H₃)heptan-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• Synonyms: (εR,1R,3aS,4E,7aR)-Octahydro-4-[(2Z)-2-[(5R)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-α,α,ε,7a-tetramethyl-H-indene-1-pentanol-d6; (3α,5Z,7E)-9,10-Seco-cholesta-5,7,10(19)-triene-3,25-diol-d6; 3-epi-25-Hydroxyvitamin D3-d6; 3-epi-25-Hydroxy Vitamin D3-d6

Database IDs

• PubChem SID: 164227363
• PubChem CID: 71749418

CALCULATED PROPERTIES

• Acid pKa: 18.384342
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.654346
• LogD (pH = 7.4): 5.654346
• Log P: 5.654346
• Molar Refractivity: 125.0606 cm^3
• Polarizability: 48.829468 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 60-62°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H995862

The labelled epimer metabolite of Calcifediol or 25-hydroxyvitamin D3 (C125700).

REFERENCES

• Sakaki, T., et al.: Eur. J. Biochem., 267, 6158 (2000)
• Kamao, M., et al.: J. Biol. Chem., 278, 1463 (2000)