(1R,3S,5Z)-5-{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}-4-methylidenecyclohexane-1,3-diol

• ChemBase ID: 167890
• Molecular Formular: C28H44O3
• Molecular Mass: 428.64716
• Monoisotopic Mass: 428.32904527
• 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)O
• Canonical SMILES: O[C@H]1C[C@H](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/C28H44O3/c1-18(9-10-19(2)27(4,5)31)24-13-14-25-21(8-7-15-28(24,25)6)11-12-22-16-23(29)17-26(30)20(22)3/h9-12,18-19,23-26,29-31H,3,7-8,13-17H2,1-2,4-6H3/b10-9+,21-11+,22-12-/t18-,19+,23-,24-,25+,26+,28-/m1/s1
• InChIKey: ZGLHBRQAEXKACO-XJRQOBMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{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}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3S,5Z)-5-{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}-4-methylidenecyclohexane-1,3-diol
• Synonyms: (1R,3S,5Z)-4-Methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R,2E)-5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol; (1α,3β,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-1,3,25-triol; 1,25-Dihydroxycalciferol; 1,25-Dihydroxyergocalciferol; Ercalcitriol; Ro 17-6218; 1α,25-Dihydroxy Vitamin D2

Database IDs

• CAS Number: 60133-18-8
• PubChem SID: 162262023
• PubChem CID: 9547243

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.353792
• LogD (pH = 7.4): 4.353792
• Log P: 4.353792
• Molar Refractivity: 132.1207 cm^3
• Polarizability: 51.0291 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D455065

The active metabolite of Vitamin D2 (V676040).

REFERENCES

• Lam, H., et al.: Science, 186, 1038 (1974)
• Dilworth, F., et al.: J. Biol. Chem., 270, 16766 (1974)
• Horst, R., et al.: Biochem. Pharmacol. 60, 701 (1974)
• Horst, R., et al.: J. Cell Biochem., 88, 282 (1974)