2-amino-4-[(1-carboxy-2-sulfanylethyl)carbamoyl]butanoic acid

• ChemBase ID: 127527
• Molecular Formular: C8H14N2O5S
• Molecular Mass: 250.27216
• Monoisotopic Mass: 250.06234256
• SMILES: NC(CCC(=O)NC(CS)C(=O)O)C(=O)O
• Canonical SMILES: SCC(C(=O)O)NC(=O)CCC(C(=O)O)N
• InChI: InChI=1S/C8H14N2O5S/c9-4(7(12)13)1-2-6(11)10-5(3-16)8(14)15/h4-5,16H,1-3,9H2,(H,10,11)(H,12,13)(H,14,15)
• InChIKey: RITKHVBHSGLULN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-4-[(1-carboxy-2-sulfanylethyl)carbamoyl]butanoic acid
• IUPAC Traditional name: 2-amino-4-[(1-carboxy-2-sulfanylethyl)carbamoyl]butanoic acid
• Synonyms: 2-Amino-5-[(1-hydroxy-1-oxo-3-sulfanylpropan-2-yl)amino]-5-oxopentanoic acid; Gamma-Glutamylcysteine

Database IDs

• CAS Number: 686-58-8
• Beilstein Number: 1729154 (2S)-2-Amino, -4-{[(-1R)-1-carboxyethyl]carbamoyl}
• PubChem SID: 162221846
• PubChem CID: 842
• CHEBI ID: 17515
• CHEMBL: 460831
• Chemspider ID: 819
• DrugBank ID: DB03408
• KEGG ID: C00669
• MeSH Name: gamma-glutamylcysteine
• Wikipedia Title: Gamma-Glutamylcysteine

CALCULATED PROPERTIES

• Acid pKa: 1.9098868
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -5.405266
• LogD (pH = 7.4): -6.9601502
• Log P: -3.772327
• Molar Refractivity: 56.3114 cm^3
• Polarizability: 22.505947 Å^3
• Polar Surface Area: 129.72 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White, opaque crystals
• Partition Coefficient: -1.168
• pKa: 2.214
• pKb: 11.783