(2S)-2-amino-3-(carbamoylamino)propanoic acid

• ChemBase ID: 138878
• Molecular Formular: C4H9N3O3
• Molecular Mass: 147.13256
• Monoisotopic Mass: 147.06439116
• SMILES: C([C@@H](C(=O)O)N)NC(=O)N
• Canonical SMILES: NC(=O)NC[C@@H](C(=O)O)N
• InChI: InChI=1S/C4H9N3O3/c5-2(3(8)9)1-7-4(6)10/h2H,1,5H2,(H,8,9)(H3,6,7,10)/t2-/m0/s1
• InChIKey: GZYFIMLSHBLMKF-REOHCLBHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-(carbamoylamino)propanoic acid
• IUPAC Traditional name: L-β-ureidoalanine
• Synonyms: L-(-)-2-Amino-3-ureidopropionic acid; L-2-Amino-3-ureidopropionic acid; Albizziin; 3-[(Aminocarbonyl)amino]-L-alanine; L-Albizziine; L-β-Ureidoalanine; NSC 132089; L-Albizziin; L-合欢氨酸; L-脲基丙氨酸; 合欢氨酸

Database IDs

• CAS Number: 1483-07-4
• MDL Number: MFCD00007952
• PubChem SID: 24888544; 162233129
• PubChem CID: 92891

CALCULATED PROPERTIES

• Acid pKa: 2.0316815
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -4.5078354
• LogD (pH = 7.4): -4.538577
• Log P: -4.5078206
• Molar Refractivity: 31.819 cm^3
• Polarizability: 12.684027 Å^3
• Polar Surface Area: 118.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >195°C (dec.); 220-223 °C (dec.)(lit.)
• Optical Rotation: [α]23/D -23.4°, c = 1 in 1 M HCl

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36

Product Information

• Purity: 98%
• Linear Formula: H2NCONHCH2CH(NH2)CO2H

DETAILS

Toronto Research Chemicals - A512000

Albizziin is a glutamase inhibitor, a glutaminyl-tRNA synthetase inhibitor as well as an intermediate in the synthesis of heterocycles. It is also a potential effector group in affinity chromatography.

REFERENCES

• Beidler, D., et al.: Biochem. Pharmacol., 58, 1067 (1999)
• Dassonneville, L., et al.: Biochemistry, 38, 7719 (1999)
• Dirsch, V., et al.: Cancer Res., 61, 5817 (1999)
• Merschjohann, K., et al.: Planta Med., 67, 623 (1999)