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

• ChemBase编号: 1603
• 分子式: C5H12N4O3
• 平均质量: 176.17378
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-4-(carbamimidamidooxy)butanoic acid
• IUPAC传统名: canavanine
• 别名: L-刀豆氨酸; L-α-Amino-γ-(guanidinooxy)-n-butyric acid; L-Canavanine; L-2-Amino-4-(Guanidinooxy)Butyric Acid

登记号

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

理论计算性质

JChem

• Acid pKa: 2.103241
• 质子受体: 7
• 质子供体: 5
• LogD (pH = 5.5): -6.407742
• LogD (pH = 7.4): -5.1360126
• Log P: -3.7018805
• 摩尔折射率: 61.2436 cm^3
• 极化性: 15.848996 Å^3
• 极化表面积: 134.45 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -3.86
• LOG S: -1.8
• 溶解度: 2.77e+00 g/l

分子性质

理化性质

• 溶解度: H2O: <100 mg/mL
• 外观: powder

安全信息

• RTECS编号: ES7002000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥98% (TLC)
• 生物来源: from Canavalia ensiformis
• Empirical Formula (Hill Notation): C5H12N4O3

详细说明

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.
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.