(2S)-2-amino-4-[(3-carboxypropyl)carbamoyl]butanoic acid

• ChemBase ID: 125417
• Molecular Formular: C9H16N2O5
• Molecular Mass: 232.23374
• Monoisotopic Mass: 232.10592162
• SMILES: N[C@@H](CCC(=O)NCCCC(=O)O)C(=O)O
• Canonical SMILES: O=C(CC[C@@H](C(=O)O)N)NCCCC(=O)O
• InChI: InChI=1S/C9H16N2O5/c10-6(9(15)16)3-4-7(12)11-5-1-2-8(13)14/h6H,1-5,10H2,(H,11,12)(H,13,14)(H,15,16)/t6-/m0/s1
• InChIKey: MKYPKZSGLSOGLL-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-[(3-carboxypropyl)carbamoyl]butanoic acid
• IUPAC Systematic name: 4-Amino-5-((3-carboxypropyl)amino)-5-oxopentanoic acid
• IUPAC Traditional name: glugaba
• Synonyms: 2-Amino-5-(3-carboxypropylamino)-5-oxopentanoic acid; 4-(Glutam-5-ylamino)butanoic acid; γ-Glutamyl-γ-aminobutyric acid; 4-(γ-Glutamylamino)butanoic acid

Database IDs

• CAS Number: 5105-96-4
• Beilstein Number: 2418119
• PubChem SID: 162219767
• PubChem CID: 23724570; 355553
• CHEBI ID: 49260
• CHEMBL: 269574
• Chemspider ID: 315618
• KEGG ID: C15767
• Wikipedia Title: 4-(γ-Glutamylamino)butanoic_acid

CALCULATED PROPERTIES

• Acid pKa: 2.2953777
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -4.9325027
• LogD (pH = 7.4): -6.6891184
• Log P: -3.852556
• Molar Refractivity: 53.5456 cm^3
• Polarizability: 21.264698 Å^3
• Polar Surface Area: 129.72 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Partition Coefficient: -1.434
• pKa: 2.223
• pKb: 11.777