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

• ChemBase ID: 167898
• 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(CO)C)C)C)C)O)O
• Canonical SMILES: OCC([C@H](/C=C/[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)C
• InChI: InChI=1S/C28H44O3/c1-18(20(3)17-29)8-9-19(2)25-12-13-26-22(7-6-14-28(25,26)5)10-11-23-15-24(30)16-27(31)21(23)4/h8-11,18-20,24-27,29-31H,4,6-7,12-17H2,1-3,5H3/b9-8+,22-10+,23-11-/t18-,19+,20?,24+,25+,26-,27-,28+/m0/s1
• InChIKey: FEVQPNVYQOMSLW-AKMIRZCQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-7-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)-7-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)-6-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol; 26-Hydroxy-Doxercalicferol; 1,26-Dihydroxycalciferol; 1α,26-Dihydroxy Vitamin D2

Database IDs

• PubChem SID: 162262031
• PubChem CID: 71316280

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.3882284
• LogD (pH = 7.4): 4.3882284
• Log P: 4.3882284
• Molar Refractivity: 132.2133 cm^3
• Polarizability: 51.0291 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D455090

Α hydroxylated metabolite of Vitamin D2 (V676040); a synthetic analog of Vitamin D.

REFERENCES

• Knudson, B., et al.: J. Biol. Chem., 124, 287 (1938)
• ;Huber, B., et al.: J. Biol. Chem., 149, 125 (1938)