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

• ChemBase ID: 173316
• Molecular Formular: C6H14N4O2
• Molecular Mass: 174.20096
• Monoisotopic Mass: 174.11167571
• SMILES: N(C(=N)NCC[C@H](N)C(=O)O)C
• Canonical SMILES: CNC(=N)NCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H14N4O2/c1-9-6(8)10-3-2-4(7)5(11)12/h4H,2-3,7H2,1H3,(H,11,12)(H3,8,9,10)/t4-/m0/s1
• InChIKey: XJPIABCWQMIHNO-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-4-(3-methylcarbamimidamido)butanoic acid
• IUPAC Traditional name: (2S)-2-amino-4-(3-methylcarbamimidamido)butanoic acid
• Synonyms: (2S)-2-Amino-4-[[imino(methylamino)methyl]amino]butanoic Acid; 4124W; Nω-Methyl L-Norarginine

Database IDs

• CAS Number: 186308-99-6
• PubChem SID: 164229226
• PubChem CID: 44398706

CALCULATED PROPERTIES

• Acid pKa: 2.3892
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -6.1761494
• LogD (pH = 7.4): -4.678921
• Log P: -3.3832755
• Molar Refractivity: 54.0531 cm^3
• Polarizability: 16.904032 Å^3
• Polar Surface Area: 111.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M288265

An L-Arginine derivative that inhibits the enzyme dimethylarginine dimethylaminohydrolase which metabolizes the endogenous nitric oxide synthase (NOS) inhibitors, NG-monomethyl-L-arginine and NG,NG-dimethyl-L-arginine, to citrulline.

REFERENCES

• MacAllister, R.J. et al.: Br. J. Pharmacol., 119, 1533 (1996)
• Wang, Y. et al.: Biochem., 48, 8624 (1996)
• Rossiter, S. et al.: J. Med. Chem., 48, 4670 (1996)