(2S)-2-amino-5-[(4-methyl-5-oxo-4,5-dihydro-1H-pyrrol-2-yl)amino]pentanoic acid

• ChemBase ID: 170823
• Molecular Formular: C10H17N3O3
• Molecular Mass: 227.26028
• Monoisotopic Mass: 227.12699142
• SMILES: [C@@H](CCCNC1=CC(C(=O)N1)C)(N)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CCCNC1=CC(C(=O)N1)C)N
• InChI: InChI=1S/C10H17N3O3/c1-6-5-8(13-9(6)14)12-4-2-3-7(11)10(15)16/h5-7,12H,2-4,11H2,1H3,(H,13,14)(H,15,16)/t6?,7-/m0/s1
• InChIKey: TTXBVYGDJQCBCQ-MLWJPKLSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-[(4-methyl-5-oxo-4,5-dihydro-1H-pyrrol-2-yl)amino]pentanoic acid
• IUPAC Traditional name: (2S)-2-amino-5-[(4-methyl-5-oxo-1,4-dihydropyrrol-2-yl)amino]pentanoic acid
• Synonyms: N5-(4,5-Dihydro-4-methyl-5-oxo-1H-imidazol-2-yl)-L-ornithine; Nδ-(5-Hydro-5-methyl-4-imidazolon-2-yl)ornithine; MG-H1; N5-(5-Hydro-5-methyl-4-imidazolon-2-yl) L-Ornithine

Database IDs

• CAS Number: 149204-50-2
• PubChem SID: 164226733
• PubChem CID: 71749152

CALCULATED PROPERTIES

• Acid pKa: 2.1207983
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -5.8754454
• LogD (pH = 7.4): -4.6138206
• Log P: -3.2630923
• Molar Refractivity: 67.9258 cm^3
• Polarizability: 22.628376 Å^3
• Polar Surface Area: 104.45 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H947635

Ornithine modification formed at high hydrostatic pressure. Novel amino acid metabolite produced by Streptomyces sp.

REFERENCES

• Lechevalier, M., et al.: Int. J. Syst. Bacteriol., 20, 435 (1970)
• Einarsson, S., et al.: Anal. Chem., 59, 1191 (1970)
• 23) Roberts, N., et al.: Clin. Chem., 47, 316 (1970)
• Ahmed, N., et al.: J. Biol. Chem., 280, 5724 (1970)