2-(3-methylbut-2-enamido)acetic acid

• ChemBase ID: 173468
• Molecular Formular: C7H11NO3
• Molecular Mass: 157.16714
• Monoisotopic Mass: 157.07389322
• SMILES: C(NC(=O)C=C(C)C)C(=O)O
• Canonical SMILES: OC(=O)CNC(=O)C=C(C)C
• InChI: InChI=1S/C7H11NO3/c1-5(2)3-6(9)8-4-7(10)11/h3H,4H2,1-2H3,(H,8,9)(H,10,11)
• InChIKey: PFWQSHXPNKRLIV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-methylbut-2-enamido)acetic acid
• IUPAC Traditional name: (3-methylbut-2-enamido)acetic acid
• Synonyms: N-(3-Methyl-1-oxo-2-butenyl)glycine; β-Methylcrotonylglycine; 3-Methylcrotonylglycine; N-(3,3-Dimethylacrylyl)glycine; 3-Methylcrotonyl Glycine

Database IDs

• CAS Number: 33008-07-0
• PubChem SID: 164229378
• PubChem CID: 169485

CALCULATED PROPERTIES

• Acid pKa: 4.0915427
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.3644704
• LogD (pH = 7.4): -3.0467732
• Log P: 0.05766032
• Molar Refractivity: 40.0504 cm^3
• Polarizability: 15.1725 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 145-147°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M294540

A metabolite found in 3-methylcrotonylglycinuria, a metabolic disorder.

REFERENCES

• Vasiliades, J., et al.: Clin. Chem., 22, 1664 (1976)
• Rinaldo, P., et al.: J. Pediatr., 122, 580 (1976)
• Bennett, M., et al.: Clin. Chim Acta, 226, 211 (1976)
• Wilcox, B., et al.: Biochemistry, 38, 3235 (1976)