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

• ChemBase ID: 167888
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C1[C@H](CCC(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](CC(CC(O)(C)C)O)C)C)O
• Canonical SMILES: OC(CC(O)(C)C)C[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC/C/2=C\C=C/1\C[C@@H](O)CCC1=C)C
• InChI: InChI=1S/C27H44O3/c1-18-8-11-22(28)16-21(18)10-9-20-7-6-14-27(5)24(12-13-25(20)27)19(2)15-23(29)17-26(3,4)30/h9-10,19,22-25,28-30H,1,6-8,11-17H2,2-5H3/b20-9+,21-10-/t19-,22+,23?,24-,25+,27-/m1/s1
• InChIKey: JVBPQHSRTHJMLM-KROKRKHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol
• IUPAC Traditional name: (6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-2-methylheptane-2,4-diol
• Synonyms: (6R)-2-Methyl-6-[(1R,3aS,4E,7aR)-octahydro-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-7a-methyl-1H-inden-1-yl]-2,4-heptanediol; (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,23,25-triol; 23,25-Dihydroxy-cholecalciferol; 23,25-Hydroxycalcidiol; 23,25-Dihydroxy Vitamin D3

Database IDs

• CAS Number: 77733-16-5
• PubChem SID: 162262021
• PubChem CID: 20839193

CALCULATED PROPERTIES

• Acid pKa: 14.929132
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.1948333
• LogD (pH = 7.4): 4.1948338
• Log P: 4.1948338
• Molar Refractivity: 126.6865 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D455050

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)