(1S,2R,3E)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,2-diol

• ChemBase ID: 167882
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: [C@@H]1([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)O
• Canonical SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C\1/C(=C)CC[C@@H]([C@@H]1O)O)CCCC(O)(C)C
• InChI: InChI=1S/C27H44O3/c1-18-10-15-24(28)25(29)21(18)12-11-20-9-7-17-27(5)22(13-14-23(20)27)19(2)8-6-16-26(3,4)30/h11-12,19,22-25,28-30H,1,6-10,13-17H2,2-5H3/b20-11+,21-12+/t19-,22-,23+,24+,25-,27-/m1/s1
• InChIKey: XJPACCVLRWWBGH-KOHSFIOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,3E)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,2-diol
• IUPAC Traditional name: (1S,2R,3E)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,2-diol
• Synonyms: (3β,4β,5E,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,4,25-triol; 4β,25-Dihydroxy Vitamin D3

Database IDs

• CAS Number: 573951-39-0
• PubChem SID: 162262015
• PubChem CID: 71316275

CALCULATED PROPERTIES

• Acid pKa: 13.453885
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.7353497
• LogD (pH = 7.4): 4.7353497
• Log P: 4.73535
• Molar Refractivity: 126.2681 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Pale Yellow Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - D455015

The 4β-metabolite of 25-Hydroxyvitamin D3 by microsomal and mitochondrial vitamin D3 25-hydroxylases (CYP2D25 and CYP27A1).

REFERENCES

• Beckman, M., et al.: Biochemistry, 35, 8465 (1996)
• Hosseinpour, F., et al.: J. Biol. Chem., 275, 34650 (1996)
• Henry, H., et al.: Steroids, 66, 391 (1996)