(2S)-5-amino-2-(methylamino)pentanoic acid hydrochloride

• ChemBase ID: 154620
• Molecular Formular: C6H15ClN2O2
• Molecular Mass: 182.6485
• Monoisotopic Mass: 182.08220541
• SMILES: CN[C@@H](CCCN)C(=O)O.Cl
• Canonical SMILES: CN[C@H](C(=O)O)CCCN.Cl
• InChI: InChI=1S/C6H14N2O2.ClH/c1-8-5(6(9)10)3-2-4-7;/h5,8H,2-4,7H2,1H3,(H,9,10);1H/t5-;/m0./s1
• InChIKey: OUPNMQRLBAANLP-JEDNCBNOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-5-amino-2-(methylamino)pentanoic acid hydrochloride
• IUPAC Traditional name: (2S)-5-amino-2-(methylamino)pentanoic acid hydrochloride
• Synonyms: (S)-5-Amino-2-(methylamino)pentanoic acid hydrochloride; N-Me-Orn-OH · HCl; Nα-Methyl-L-ornithine monohydrochloride

Database IDs

• CAS Number: 37148-99-5
• MDL Number: MFCD03093490
• Beilstein Number: 6117952
• PubChem SID: 162248758
• PubChem CID: 56845422

CALCULATED PROPERTIES

• Acid pKa: 2.3009076
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -6.211507
• LogD (pH = 7.4): -5.633015
• Log P: -3.4720433
• Molar Refractivity: 37.9831 cm^3
• Polarizability: 15.365045 Å^3
• Polar Surface Area: 75.35 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Optical Rotation: [α]/D +27.0±1.0°, c = 1 in 1 M HCl

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338

Product Information

• Purity: ≥98% (TLC)
• Compostion: carbon, 38.7-40.2%; nitrogen, 14.9-15.7%
• Empirical Formula (Hill Notation): C6H14N2O2 · HCl

DETAILS

Sigma Aldrich - 18726

Biochem/physiol Actions
Nα-Methyl-L-ornithine has been identified as an inhibitor of nitric oxidase synthase in macrophages. 1