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

• ChemBase ID: 133321
• Molecular Formular: C5H14N4O7S
• Molecular Mass: 274.25226
• Monoisotopic Mass: 274.05831981
• SMILES: C(CONC(=N)N)[C@@H](C(=O)O)N.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.NC(=N)NOCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H12N4O3.H2O4S/c6-3(4(10)11)1-2-12-9-5(7)8;1-5(2,3)4/h3H,1-2,6H2,(H,10,11)(H4,7,8,9);(H2,1,2,3,4)/t3-;/m0./s1
• InChIKey: MVIPJKVMOKFIEV-DFWYDOINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(carbamimidamidooxy)butanoic acid; sulfuric acid
• IUPAC Traditional name: canavanine; sulfuric acid
• Synonyms: L-Canavanine sulfate salt; L-α-Amino-γ-(guanidinooxy)butyric acid sulfate salt; 4-胍氧丁胺酸 硫酸盐; L-刀豆氨酸 硫酸盐

Database IDs

• CAS Number: 2219-31-0
• EC Number: 218-728-4
• MDL Number: MFCD00012618
• Beilstein Number: 6121291
• PubChem SID: 24278349; 24852798; 162227598
• PubChem CID: 11957500

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: H2O: soluble100 mg/mL
• Apperance: white powder
• Melting Point: 160-165 °C (dec.)
• Optical Rotation: [α]20/D +17±1°, c = 2% in H2O

Safety Information

• 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

Pharmacology Properties

• Gene Information: human ... NOS2(4843)

Product Information

• Purity: ≥98.0% (TLC); ≥99% (TLC)
• Empirical Formula (Hill Notation): C5H12N4O3 · H2SO4

DETAILS

Sigma Aldrich - C9758

Biochem/physiol Actions
天然存在的 L-氨基酸会干扰 L-精氨酸利用酶，原因是它与该 L-氨基酸结构相似。它是诱导型一氧化氮合成酶 (iNOS) 的选择性抑制剂。

Sigma Aldrich - 21375

Other Notes
A structural analog of L-arginine. Review: Biological effects and mode of action1
Biochem/physiol Actions
Naturally occurring L-amino acid that interferes with L-arginine-utilizing enzymes due to its structural similarity with this L-amino acid. It is a selective inhibitor of inducible nitric oxide synthase (iNOS).