(2S)-2-amino-5-(3-propylcarbamimidamido)pentanoic acid

• ChemBase ID: 2370
• Molecular Formular: C9H20N4O2
• Molecular Mass: 216.2807
• Monoisotopic Mass: 216.1586259
• SMILES: CCCNC(=N)NCCC[C@H](N)C(=O)O
• Canonical SMILES: CCCNC(=N)NCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C9H20N4O2/c1-2-5-12-9(11)13-6-3-4-7(10)8(14)15/h7H,2-6,10H2,1H3,(H,14,15)(H3,11,12,13)/t7-/m0/s1
• InChIKey: AOMXURITGZJPKB-ZETCQYMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(3-propylcarbamimidamido)pentanoic acid; (2S)-2-amino-5-(1-propylcarbamimidamido)pentanoic acid
• IUPAC Traditional name: (2S)-2-amino-5-(3-propylcarbamimidamido)pentanoic acid; (2S)-2-amino-5-(1-propylcarbamimidamido)pentanoic acid
• Synonyms: N-Omega-Propyl-L-Arginine; 2-Amino-5-[(N'-propylcarbamimidoyl)amino]pentanoic acid; N-Propyl-L-arginine; N5-[Imino(propylamino)methyl]-L-ornithine; Nω-Propyl-L-Arginine

Database IDs

• CAS Number: 137361-05-8
• PubChem SID: 160965821; 46507586
• PubChem CID: 4387; 447180; 5287494
• CHEMBL: 126713
• Chemspider ID: 4234
• Wikipedia Title: N-Propyl-L-arginine

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.286612
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.9100637
• LogD (pH = 7.4): -3.6868277
• Log P: -1.990613
• Molar Refractivity: 67.9703 cm^3
• Polarizability: 22.384264 Å^3
• Polar Surface Area: 111.23 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.06
• LOG S: -1.7
• Solubility (Water): 4.99e+00 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 198-200°C
• Partition Coefficient: 0.389
• pKa: 2.512
• pKb: 11.485

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB02644

Drug information: experimental

Toronto Research Chemicals - P835000

A highly selective competitive inhibitor and inactivator of all three isoforms of NOS.

REFERENCES

• Marletta, M.A.: J. Med. Chem., 37(13)
• 1899 (13)
• Zhang, H.Q., et al.: J. Med. Chem., 40, 3869 (1997)