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

• ChemBase ID: 4342
• Molecular Formular: C27H40O3
• Molecular Mass: 412.6047
• Monoisotopic Mass: 412.29774514
• SMILES: O[C@H]1C[C@@H](C(=C)/C(=C\C=C/2\CCC[C@]3([C@@H]2CC[C@@H]3[C@H](C)CC#CC(C)(C)O)C)/C1)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](CC#CC(O)(C)C)C)C)/C1
• InChI: InChI=1S/C27H40O3/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,2,7-9,12-13,15-17H2,1,3-5H3/b20-10-,21-11-/t18-,22-,23-,24-,25+,27-/m1/s1
• InChIKey: BUDPDEVHCQIFNU-PUBYVPDWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{2-[(1R,3aR,4Z,7aR)-1-[(2R)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3S,5Z)-5-{2-[(1R,3aR,4Z,7aR)-1-[(2R)-6-hydroxy-6-methylhept-4-yn-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• Synonyms: TX522; 19-nor-14-epi-23-yne-1,25 dihydroxyvitamin D3

Database IDs

• PubChem SID: 46504586; 160967774
• PubChem CID: 46937021

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.333249
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.0913553
• LogD (pH = 7.4): 4.091355
• Log P: 4.0913553
• Molar Refractivity: 125.7399 cm^3
• Polarizability: 48.31969 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 5.15
• LOG S: -5.2
• Solubility (Water): 2.58e-03 g/l

DETAILS

DrugBank - DB04796

• Drug Groups: experimental
• Indication: Investigated for use/treatment in prostate cancer, psoriasis and hyperparathyroidism.
• References: Wong MS, Delansorne R, Man RY, Vanhoutte PM: Vitamin D derivatives acutely reduces endothelium-dependent contractions in the aorta of the spontaneously hypertensive rat. Am J Physiol Heart Circ Physiol. 2008 May 16;. [Pubmed] ; Eelen G, Verlinden L, Van Camp M, Claessens F, De Clercq P, Vandewalle M, Bouillon R, Verstuyf A: Altered Vitamin D receptor-coactivator interactions reflect superagonism of Vitamin D analogs. J Steroid Biochem Mol Biol. 2005 Oct;97(1-2):65-8. Epub 2005 Jul 20. [Pubmed] ; Company Website [Link]

REFERENCES

• Wong MS, Delansorne R, Man RY, Vanhoutte PM: Vitamin D derivatives acutely reduces endothelium-dependent contractions in the aorta of the spontaneously hypertensive rat. Am J Physiol Heart Circ Physiol. 2008 May 16;. Pubmed
• Eelen G, Verlinden L, Van Camp M, Claessens F, De Clercq P, Vandewalle M, Bouillon R, Verstuyf A: Altered Vitamin D receptor-coactivator interactions reflect superagonism of Vitamin D analogs. J Steroid Biochem Mol Biol. 2005 Oct;97(1-2):65-8. Epub 2005 Jul 20. Pubmed
• Company Website Link