1-[4-(4-{[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

• ChemBase ID: 172057
• Molecular Formular: C26H28Cl2N4O4
• Molecular Mass: 531.43092
• Monoisotopic Mass: 530.14876076
• SMILES: C1N(CCN(C1)c1ccc(cc1)OC[C@@H]1CO[C@@](O1)(c1ccc(cc1Cl)Cl)Cn1cncc1)C(=O)C
• Canonical SMILES: Clc1ccc(c(c1)Cl)[C@]1(OC[C@H](O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
• InChI: InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26+/m1/s1
• InChIKey: XMAYWYJOQHXEEK-BVAGGSTKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(4-{[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
• IUPAC Traditional name: (2R,4R)-ketoconazole
• Synonyms: rel-1-Acetyl-4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; trans-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; R 44319; RS 36745; rac-trans-Ketoconazole

Database IDs

• CAS Number: 83374-59-8
• PubChem SID: 164227967
• PubChem CID: 12854713

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.6516862
• LogD (pH = 7.4): 4.128518
• Log P: 4.191598
• Molar Refractivity: 138.0672 cm^3
• Polarizability: 53.26531 Å^3
• Polar Surface Area: 69.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - K186010

Ketoconazole (K186000) analog. The trans isomer of Ketoconazole.

REFERENCES

• Kan, P.B., et al.: J. Steroid Biochem., 23, 1023 (1985)