(1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-7-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol

• ChemBase ID: 167887
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• 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](CCCC(CO)C)C)C)O)O
• Canonical SMILES: OCC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C/1\C[C@@H](O)C[C@@H](C1=C)O)C)C
• InChI: InChI=1S/C27H44O3/c1-18(17-28)7-5-8-19(2)24-12-13-25-21(9-6-14-27(24,25)4)10-11-22-15-23(29)16-26(30)20(22)3/h10-11,18-19,23-26,28-30H,3,5-9,12-17H2,1-2,4H3/b21-10+,22-11-/t18?,19-,23-,24-,25+,26+,27-/m1/s1
• InChIKey: LTDVBAXFIVSUFW-IQLPMBEJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-7-hydroxy-6-methylheptan-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)-7-hydroxy-6-methylheptan-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• Synonyms: (1α,3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,26-triol; 1α,26-Dihydroxy Vitamin D3

Database IDs

• CAS Number: 300692-92-6
• PubChem SID: 162262020
• PubChem CID: 71316277

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.463131
• LogD (pH = 7.4): 4.463131
• Log P: 4.463131
• Molar Refractivity: 126.5481 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D455045

Α hydroxylated metabolite of Vitamin D3 (V676045).

REFERENCES

• Gray, R., et al.: Biochem. J., 259, 561 (1989)
• Sakaki, T., et al.: J. Biol. Chem., 271, 26209 (1989)
• Takeyama, K., et al.: Science, 277, 1827 (1989)