6-{4-[1-(4-hydroxycyclohexyl)-1H-1,2,3,4-tetrazol-5-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one

• ChemBase ID: 170353
• Molecular Formular: C20H27N5O3
• Molecular Mass: 385.46008
• Monoisotopic Mass: 385.21138975
• SMILES: c1cc(cc2c1NC(=O)CC2)OCCCCc1nnnn1C1CC[C@@H](CC1)O
• Canonical SMILES: O[C@@H]1CCC(CC1)n1nnnc1CCCCOc1ccc2c(c1)CCC(=O)N2
• InChI: InChI=1S/C20H27N5O3/c26-16-7-5-15(6-8-16)25-19(22-23-24-25)3-1-2-12-28-17-9-10-18-14(13-17)4-11-20(27)21-18/h9-10,13,15-16,26H,1-8,11-12H2,(H,21,27)/t15?,16-
• InChIKey: KFXNZXLUGHLDBB-CXIWYSOXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{4-[1-(4-hydroxycyclohexyl)-1H-1,2,3,4-tetrazol-5-yl]butoxy}-1,2,3,4-tetrahydroquinolin-2-one
• IUPAC Traditional name: 6-{4-[1-(4-hydroxycyclohexyl)-1,2,3,4-tetrazol-5-yl]butoxy}-3,4-dihydro-1H-quinolin-2-one
• Synonyms: trans-3,4-Dihydro-6-[4-[1-(4-hydroxycyclohexyl)-1H-tetrazol-5-yl]butoxy]-2(1H)-quinolinone; OPC 13213; 4''-trans-Hydroxy Cilostazol

Database IDs

• CAS Number: 87153-04-6
• PubChem SID: 164226263
• PubChem CID: 10022985

CALCULATED PROPERTIES

• Acid pKa: 14.357561
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.9188472
• LogD (pH = 7.4): 1.9188476
• Log P: 1.9188477
• Molar Refractivity: 118.8044 cm^3
• Polarizability: 39.84224 Å^3
• Polar Surface Area: 102.16 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform (Sparingly); DMSO; Ethanol (Sparingly)
• Apperance: White to Off-White Solid
• Melting Point: 200-202°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H918300

A metabolite of Cilostazol.

REFERENCES

• de Morais, S., et al.: J. Biol. Chem., 269, 15419 (1994)
• Tata, P; J Pharm Biomed Anal 2001, 24, 381,Hiratsuka, M; Eur J Clin Pharmacol 2002, 58, 417,,Roy, J; Drug Metab Dispos 2005, 33, 884