(2S)-2-amino-3-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]propanoic acid

• ChemBase ID: 134124
• Molecular Formular: C14H14N2O5
• Molecular Mass: 290.27136
• Monoisotopic Mass: 290.09027156
• SMILES: Cc1cc(=O)oc2c1ccc(c2)NC(=O)C[C@@H](C(=O)O)N
• Canonical SMILES: O=C(C[C@@H](C(=O)O)N)Nc1ccc2c(c1)oc(=O)cc2C
• InChI: InChI=1S/C14H14N2O5/c1-7-4-13(18)21-11-5-8(2-3-9(7)11)16-12(17)6-10(15)14(19)20/h2-5,10H,6,15H2,1H3,(H,16,17)(H,19,20)/t10-/m0/s1
• InChIKey: ARZPQBJTLVVDNP-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-[(4-methyl-2-oxo-2H-chromen-7-yl)carbamoyl]propanoic acid
• IUPAC Traditional name: (2S)-2-amino-3-[(4-methyl-2-oxochromen-7-yl)carbamoyl]propanoic acid
• Synonyms: L-Aspartic acid β-(4-methyl-7-coumarinylamide); L-Aspartic acid 4-(4-methyl-7-coumarinylamide); L-Aspartic acid β-(7-amido-4-methylcoumarin)

Database IDs

• CAS Number: 133628-73-6
• MDL Number: MFCD00236804
• PubChem SID: 162228401; 24890500
• PubChem CID: 688365

CALCULATED PROPERTIES

• Acid pKa: 1.4732951
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9389931
• LogD (pH = 7.4): -1.9748203
• Log P: -1.9387387
• Molar Refractivity: 74.5826 cm^3
• Polarizability: 28.221514 Å^3
• Polar Surface Area: 118.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A1057

Biochem/physiol Actions
L-Aspartic acid-β-7-amido-4-methylcoumarin is sensitive and specific fluorogenic substrate used to assay for lysosomal glycoasparaginase (aspartylglucosaminidase) activity and the diagnosis of aspartylglucosaminuria.