5-[(2R)-5-cyclohexyl-1-(hydroxycarbamoyl)pentan-2-yl]-1,2,4-oxadiazole-3-carboxamide

• ChemBase ID: 72910
• Molecular Formular: C15H24N4O4
• Molecular Mass: 324.37546
• Monoisotopic Mass: 324.17975527
• SMILES: C1C(CCCC1)CCC[C@@H](c1nc(no1)C(=O)N)CC(=O)NO
• Canonical SMILES: ONC(=O)C[C@H](c1onc(n1)C(=O)N)CCCC1CCCCC1
• InChI: InChI=1S/C15H24N4O4/c16-13(21)14-17-15(23-19-14)11(9-12(20)18-22)8-4-7-10-5-2-1-3-6-10/h10-11,22H,1-9H2,(H2,16,21)(H,18,20)/t11-/m1/s1
• InChIKey: ARJCBSRIPGJMAD-LLVKDONJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(2R)-5-cyclohexyl-1-(hydroxycarbamoyl)pentan-2-yl]-1,2,4-oxadiazole-3-carboxamide
• IUPAC Traditional name: 5-[(2R)-5-cyclohexyl-1-(hydroxycarbamoyl)pentan-2-yl]-1,2,4-oxadiazole-3-carboxamide
• Synonyms: 5-[(1R)-4-Cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl]-1,2,4-oxadiazole-3-carboxamide; UK 383367; PF-04171426; UK-383367; 5-{(1R)-4-Cyclohexyl-1-[2-(hydroxyamino)-2-oxoethyl]butyl}-1,2,4-oxadiazole-3-carboxamide; (βR)-3-(Aminocarbonyl)-β-(3-cyclohexylpropyl)-N-hydroxy-1,2,4-oxadiazole-5-propanamide; UK-383,367; UK-383367; UK 383367

Database IDs

• CAS Number: 348622-88-8
• PubChem SID: 162037830
• PubChem CID: 9818682

CALCULATED PROPERTIES

• Acid pKa: 8.899457
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6708186
• LogD (pH = 7.4): 1.6575282
• Log P: 1.6709907
• Molar Refractivity: 83.8621 cm^3
• Polarizability: 31.617924 Å^3
• Polar Surface Area: 131.34 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >30 mg/mL
• Apperance: white to off-white powder
• Optical Rotation: [α]/D ≥15°, c = 0.5 in methanol

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Storage Temperature: room temp

Pharmacology Properties

• Target: Procollagen C Proteinase

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H24N4O4

DETAILS

Selleck Chemicals - S2224

Related research area: Cancer

Sigma Aldrich - PZ0156

Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
UK-383,367 is a procollagen C-proteinase (PCP) inhibitor.

Toronto Research Chemicals - U700600

Potent and selective nonpeptidic inhibitor of procollagen C-proteinase (PCP) inhibitor. A potential dermal anti-scarring agent.

REFERENCES

• Allan GA et al. Xenobiotica. 2006 May; 36(5):399-418.
• Fish, P.V. et al.: J. Med. Chem., 50, 3442 (2007)
• Allan, G.A. et al.: Xenobiotica, 36, 399 (2007)
• Bailey, S. et al.: Biorog. Med. Chem. Lett., 18, 6562 (2007)