(1R,3S,5E)-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: 163541
• Molecular Formular: C27H40O3
• Molecular Mass: 412.6047
• Monoisotopic Mass: 412.29774514
• SMILES: C(=C\1/CCC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@H](C1CC1)O)C)C)/C=C\1/C(=C)[C@H](C[C@@H](C1)O)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-GMGGYIQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5E)-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: (1R,3S,5E)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• Synonyms: (1S,3S,5E)-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; 5,6-trans-Calcipotriol; PRI 2205; (1α,3β,5E,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol; (5E)-Calcipotriene

Database IDs

• CAS Number: 113082-99-8
• PubChem SID: 162257676
• PubChem CID: 9801803

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

DETAILS

Toronto Research Chemicals - C144210

The trans-isomeric impurity of Calcipotriene (C144200) and a vitamin D3 analogue with antitumor effects.

REFERENCES

• Wietrzyk, J. et al.: Anti-Cancer Drugs, 18, 447 (2007)
• Wietrzyk, J. et al.: Anticancer Res., 27, 3387 (2007)
• Filip, B. et al.: J. Ster. Biochem. Mol. Biol., 121, 399 (2007)