(2S)-2-amino-4-(carbamimidamidooxy)butanoic acid

• ChemBase ID: 1603
• Molecular Formular: C5H12N4O3
• Molecular Mass: 176.17378
• Monoisotopic Mass: 176.09094026
• SMILES: N[C@@H](CCONC(=N)N)C(=O)O
• Canonical SMILES: NC(=N)NOCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1
• InChIKey: FSBIGDSBMBYOPN-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(carbamimidamidooxy)butanoic acid
• IUPAC Traditional name: canavanine
• Synonyms: L-α-Amino-γ-(guanidinooxy)-n-butyric acid; L-Canavanine; L-2-Amino-4-(Guanidinooxy)Butyric Acid; L-刀豆氨酸

Database IDs

• CAS Number: 543-38-4
• MDL Number: MFCD00055781
• PubChem SID: 24892427; 160965060; 46507101
• PubChem CID: 439202

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.103241
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -6.407742
• LogD (pH = 7.4): -5.1360126
• Log P: -3.7018805
• Molar Refractivity: 61.2436 cm^3
• Polarizability: 15.848996 Å^3
• Polar Surface Area: 134.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.86
• LOG S: -1.8
• Solubility (Water): 2.77e+00 g/l

PROPERTIES

Physical Property

• Solubility: H2O: <100 mg/mL
• Apperance: powder

Safety Information

• RTECS: ES7002000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)
• Biological Source: from Canavalia ensiformis
• Empirical Formula (Hill Notation): C5H12N4O3

DETAILS

DrugBank - DB01833

Drug information: experimental

Sigma Aldrich - C1625

Biochem/physiol Actions
A naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). Overproduction of NO by iNOS plays a crucial role in the pathophysiology of septic shock and chronic inflammation.
Canavanine is a naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity. It is a selective inhibitor of inducible nitric oxide synthase (iNOS). Overproduction of NO by iNOS plays a crucial role in the pathophysiology of septic shock and chronic inflammation.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.