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

• ChemBase ID: 167893
• 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](CCCC(CO)(O)C)C)C)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)CCC1=C)C)(O)C
• InChI: InChI=1S/C27H44O3/c1-19-9-12-23(29)17-22(19)11-10-21-8-6-16-27(4)24(13-14-25(21)27)20(2)7-5-15-26(3,30)18-28/h10-11,20,23-25,28-30H,1,5-9,12-18H2,2-4H3/b21-10+,22-11-/t20-,23+,24-,25+,26?,27-/m1/s1
• InChIKey: QOWCBCXATJITSI-ZLNGONTQSA-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-1,2-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-1,2-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]-1,2-Heptanediol; (3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-3,25,26-triol; 9,10-Secocholesta-5,7,10(19)-triene-3β,25,26-triol; 25,26-Dihydroxycholecalciferol; 25,26-Dihydroxyvitamin D; 25,26-Dihydroxy Vitamin D3

Database IDs

• CAS Number: 29261-12-9
• PubChem SID: 162262026
• PubChem CID: 21159907

CALCULATED PROPERTIES

• Acid pKa: 14.038376
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.607436
• LogD (pH = 7.4): 4.607436
• Log P: 4.607436
• Molar Refractivity: 126.6043 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 - D455075

Α hydroxylated metabolite of Vitamin D3 (V676045).

REFERENCES

• Sawada, N. et al.: Biochem. Biophys. Res. Comm., 273, 977 (2000)
• Tornquist, K. et al.: J. Endocrin. Inv., 13, 391 (2000)
• Hoogenboezem, T. et al.: Ped. Res., 25, 623 (2000)