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

• ChemBase ID: 177721
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C1C/C(=C\C=C/2\C[C@H](CCC2=C)O)/[C@H]2[C@](C1)([C@H](CC2)[C@@H](CC[C@H](C(C)(O)C)O)C)C
• Canonical SMILES: O[C@H]1CCC(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CC[C@H](C(O)(C)C)O)C)C)/C1
• InChI: InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22+,23-,24+,25-,27-/m1/s1
• InChIKey: FCKJYANJHNLEEP-XRWYNYHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
• IUPAC Traditional name: secalciferol
• Synonyms: K-DR; Osteo D; Secalciferol; (3R,6R)-2-Methyl-6-[(1R,3aS,4E,7aR)-octahydro-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-7a-methyl-1H-inden-1-yl]-2,3-heptanediol; (3β,5Z,7E,24R)-9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triol; PRI 1201; (24R)-Hydroxycalcidiol; 24R,25-Dihydroxyvitamin D3

Database IDs

• CAS Number: 55721-11-4
• PubChem SID: 164233631
• PubChem CID: 5283748

CALCULATED PROPERTIES

• H Donor: 3
• LogD (pH = 5.5): 4.5794425
• LogD (pH = 7.4): 4.5794425
• Log P: 4.5794425
• Molar Refractivity: 126.4221 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true
• Acid pKa: 13.849643
• H Acceptors: 3

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 56-58°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S211500

A metabolite of Vitamin D, a possibly anti-inflammatory steroid.

REFERENCES

• Boyan, B., et al.: Steroids, 66, 363 (2001)
• Holick, M., et al.: J. Cell Biochem., 88, 296 (2001)
• Vogeser, M., et al.: Clin. Chem., 50, 1415 (2001)
• Singh, R., et al.: J. Clin. Endocrinol. Metab., 91, 3055 (2001)