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

• ChemBase ID: 163539
• Molecular Formular: C27H40O3
• Molecular Mass: 412.6047
• Monoisotopic Mass: 412.29774514
• SMILES: C1[C@@H](C(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@H](C2CC2)O)C)C)/C[C@H]1O)O
• 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](/C=C/[C@H](C2CC2)O)C)C)/C1
• InChI: InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
• InChIKey: LWQQLNNNIPYSNX-UROSTWAQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: calcipotriol
• Synonyms: (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,2E,4S)-4-Cyclopropyl-4-hydroxy-1-methyl-2-buten-1-yl]octahydro-7a-methyl-4H-inden-4-ylidene]ethylidene]-4-methylene-1,3-cyclohexanediol; Calciptriol, MC-903, Daivonex, Dovonex, Psorcutan; Calcipotriene

Database IDs

• CAS Number: 112965-21-6
• PubChem SID: 162257674
• PubChem CID: 5288783

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.8433506
• LogD (pH = 7.4): 3.8433506
• Log P: 3.843351
• Molar Refractivity: 125.4493 cm^3
• Polarizability: 48.449245 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 156-162°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C144200

An antipsoriatic. A vitamin D3 analogue with low calcemic activity.

REFERENCES

• Binderup, L. and Bramm, E.: Biochem. Pharmacol., 37, 889 (1988)
• Valaja, T., et al.: Biochem. Pharmacol., 40, 1827 (1988)
• Ashcroft, D.M., et al.: Brit Med. J., 320, 963 (1988)
• Ghoreishi, M., et al.: J. Immunol., 182, 6071 (1988)
• Sato, T., et al.: J. Me