(2S)-2-amino-4-(3-hydroxycarbamimidamido)butanoic acid

• ChemBase编号: 2122
• 分子式: C5H12N4O3
• 平均质量: 176.17378
• 单一同位素质量: 176.09094026
• SMILES: N[C@@H](CCNC(=N)NO)C(=O)O
• Canonical SMILES: ONC(=N)NCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-8-5(7)9-12/h3,12H,1-2,6H2,(H,10,11)(H3,7,8,9)/t3-/m0/s1
• InChIKey: KOBHCUDVWOTEKO-VKHMYHEASA-N

名称和登记号

名称

• IUPAC标准名: (2S)-2-amino-4-(3-hydroxycarbamimidamido)butanoic acid; (2S)-2-amino-4-(1-hydroxycarbamimidamido)butanoic acid
• IUPAC传统名: (2S)-2-amino-4-(3-hydroxycarbamimidamido)butanoic acid; @nor-N-ω-hydroxy-L-arginine
• 别名: (2S)-2-Amino-4-[[(hydroxyamino)iminomethyl]amino]butanoic Acid; nor-NOHA; Nω-Hydroxy-nor-L-Arginine Dihydrochloride; Nor-N-Omega-Hydroxy-L-Arginine

登记号

• CAS号: 291758-32-2
• PubChem SID: 160965576; 46505343
• PubChem CID: 446124

理论计算性质

JChem

• Acid pKa: 2.081529
• 质子受体: 7
• 质子供体: 6
• LogD (pH = 5.5): -6.394319
• LogD (pH = 7.4): -4.898132
• Log P: -3.715716
• 摩尔折射率: 61.5359 cm^3
• 极化性: 15.783365 Å^3
• 极化表面积: 131.46 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: -3.62
• LOG S: -1.9
• 溶解度: 2.24e+00 g/l

详细说明

DrugBank - DB02381

Drug information: experimental

Toronto Research Chemicals - H948800

A reversible, competitive inhibitor of arginase. It is neither a substrate nor an inhibitor for iNOS and it appears as a useful tool to study the interplays between arginase and NOS. Was found to be much more potent than NOHA and homo-NOHA to inhibit the

参考文献

• Kerwin, J., et al.: J. Med. Chem., 38, 4343 (1995)
• Wu, G., et al.: Biochem. J., 336, 1 (1995)
• Moali, C., et al.: Biochemistry, 39, 8208 (1995)