(1R,3R)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-6-(2H3)methyl-5-methyl(7,7,7-2H3)hept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}cyclohexane-1,3-diol

• ChemBase ID: 176160
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C1[C@H](C[C@@H](C/C/1=C\C=C\1/CCC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(O)(C)C)C)C)C)O)O
• Canonical SMILES: O[C@H]1C[C@H](O)C/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](C(O)(C)C)C)C)C)/C1
• InChI: InChI=1S/C27H44O3/c1-18(8-9-19(2)26(3,4)30)24-12-13-25-21(7-6-14-27(24,25)5)11-10-20-15-22(28)17-23(29)16-20/h8-11,18-19,22-25,28-30H,6-7,12-17H2,1-5H3/b9-8+,21-11+/t18-,19+,22-,23-,24-,25+,27-/m1/s1
• InChIKey: BPKAHTKRCLCHEA-UBFJEZKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3R)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-6-(^2H₃)methyl-5-methyl(7,7,7-^2H₃)hept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}cyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3R)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-6-(^2H₃)methyl-5-methyl(7,7,7-^2H₃)hept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}cyclohexane-1,3-diol
• Synonyms: (1R,3R,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-Octahydro-1-[(1R,2E,4S)-5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol-d6; (1α,3β,7E,22E)-19-Nor-9,10-secoergosta-5,7,22-triene-1,3,25-triol-d6; 19-Nor-1,25-dihydroxyvitamin D2-d6; 1α,25-Dihydroxy-19-nor-vitamin D2-d6; Zemplar-d6; Paricalcitol-d6

Database IDs

• PubChem SID: 164232070
• PubChem CID: 66577066

CALCULATED PROPERTIES

• Acid pKa: 14.811643
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.2585115
• LogD (pH = 7.4): 4.2585115
• Log P: 4.2585115
• Molar Refractivity: 127.9486 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

DETAILS

Toronto Research Chemicals - P195302

Labelled Paricalcitol (P195300). Synthetic analog of vitamin D. Antihyperparathyroid.

REFERENCES

• Sidek, H., et al.: Biochim. Biophys. Acta, 801, 26 (1984)
• Ciftci, M., et al.: J. Pharmacol., 54, 275 (1984)