1-(butan-2-yl)-4-{4-[4-(4-{[(2R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one

• ChemBase ID: 172002
• Molecular Formular: C35H38Cl2N8O4
• Molecular Mass: 705.63342
• Monoisotopic Mass: 704.2393071
• SMILES: c1(ccc(cc1Cl)Cl)[C@]1(OCC(O1)COc1ccc(cc1)N1CCN(CC1)c1ccc(cc1)n1cnn(c1=O)C(CC)C)Cn1cncn1
• Canonical SMILES: CCC(n1ncn(c1=O)c1ccc(cc1)N1CCN(CC1)c1ccc(cc1)OCC1CO[C@](O1)(Cn1cncn1)c1ccc(cc1Cl)Cl)C
• InChI: InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31?,35-/m0/s1
• InChIKey: VHVPQPYKVGDNFY-WSTHBRJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(butan-2-yl)-4-{4-[4-(4-{[(2R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one
• IUPAC Traditional name: 4-{4-[4-(4-{[(2R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2-(sec-butyl)-1,2,4-triazol-3-one
• Synonyms: rel-4-[4-[4-[4-[[(2R,4R)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one; trans-Itraconazole

Database IDs

• CAS Number: 252964-65-1
• PubChem SID: 164227912
• PubChem CID: 58612883

CALCULATED PROPERTIES

• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 7.3001556
• LogD (pH = 7.4): 7.3112283
• Log P: 7.3113713
• Molar Refractivity: 200.4 cm^3
• Polarizability: 71.596016 Å^3
• Polar Surface Area: 100.79 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I937505

A geometrical isomer of Itraconazole (I937500).

REFERENCES

• Ahn, C., et al.: J. Korean Chem. Soc., 43, 676 (1999)