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

• ChemBase ID: 2122
• Molecular Formular: C5H12N4O3
• Molecular Mass: 176.17378
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.081529
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -6.394319
• LogD (pH = 7.4): -4.898132
• Log P: -3.715716
• Molar Refractivity: 61.5359 cm^3
• Polarizability: 15.783365 Å^3
• Polar Surface Area: 131.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -3.62
• LOG S: -1.9
• Solubility (Water): 2.24e+00 g/l

DETAILS

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

REFERENCES

• 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)