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

• ChemBase ID: 163543
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C1C/C(=C\C=C/2\C[C@H](C[C@H](C2=C)O)O)/[C@H]2[C@](C1)([C@H](CC2)[C@@H](CCCC(O)(C)C)C)C
• 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](CCCC(O)(C)C)C)C)/C1
• InChI: InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25-,27-/m1/s1
• InChIKey: GMRQFYUYWCNGIN-PEJFXWBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3R,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• Synonyms: (1β,3β,5Z,7E)-9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol; 1-Epicalcitriol; 1β,25-Dihydroxycholecalciferol; 1β,25-Dihydroxyvitamin-D3; NS 8; 1-epi-Calcitriol

Database IDs

• CAS Number: 66791-71-7
• PubChem SID: 162257678
• PubChem CID: 5283741

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.350741
• LogD (pH = 7.4): 4.350741
• Log P: 4.350741
• Molar Refractivity: 126.5325 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 - C144490

An impurity of Calcitriol (C144500).

REFERENCES

• Myrtle, J.F., et al.: J. Biol. Chem., 245, 1190 (1970)
• Lawson, D.E.M., et al.: Nature, 230, 228 (1970)
• Norman, A.W., et al.: Science, 173, 51 (1970)
• Suda, T., et al.: Vitamins, 45, 175 (1970)
• Muindi, J.R., et al.: Clin. Pharmacol. Ther., 72, 648 (2002