2-{2-[(1-hydroxybut-3-en-2-yl)amino]-3-methylbutanamido}-4-methyl-N-phenylpentanamide

• ChemBase ID: 170290
• Molecular Formular: C21H33N3O3
• Molecular Mass: 375.50502
• Monoisotopic Mass: 375.25219193
• SMILES: N(C(=O)C(NC(=O)C(NC(C=C)CO)C(C)C)CC(C)C)c1ccccc1
• Canonical SMILES: OCC(NC(C(=O)NC(C(=O)Nc1ccccc1)CC(C)C)C(C)C)C=C
• InChI: InChI=1S/C21H33N3O3/c1-6-16(13-25)22-19(15(4)5)21(27)24-18(12-14(2)3)20(26)23-17-10-8-7-9-11-17/h6-11,14-16,18-19,22,25H,1,12-13H2,2-5H3,(H,23,26)(H,24,27)
• InChIKey: YVIWGLISZALAAO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(1-hydroxybut-3-en-2-yl)amino]-3-methylbutanamido}-4-methyl-N-phenylpentanamide
• IUPAC Traditional name: 2-{2-[(1-hydroxybut-3-en-2-yl)amino]-3-methylbutanamido}-4-methyl-N-phenylpentanamide
• Synonyms: (R,S)-N-2-(1-Hydroxy-3-butenyl)-L-val-L-leu phenylamide; (R,S)-N-2-(1-Hydroxy-3-butenyl)-L-valinyl-L-leucinyl Anilide

Database IDs

• PubChem SID: 164226200
• PubChem CID: 45039411

CALCULATED PROPERTIES

• Acid pKa: 12.691187
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.70990485
• LogD (pH = 7.4): 2.4256477
• Log P: 2.9941723
• Molar Refractivity: 108.641 cm^3
• Polarizability: 42.261086 Å^3
• Polar Surface Area: 90.46 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Ethanol; Ethyl Acetate; Toluene
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - H830050

A standard for the analysis of butadiene metabolites.

REFERENCES

• Begemann, P., et al.: Arch. Toxicol., 74, 680 (2001)