(2S)-2-amino-5-(3-hydroxycarbamimidamido)pentanoic acid; acetic acid

• ChemBase ID: 105653
• Molecular Formular: C8H18N4O5
• Molecular Mass: 250.25232
• Monoisotopic Mass: 250.1277197
• SMILES: CC(=O)O.N[C@@H](CCCNC(=N)NO)C(=O)O
• Canonical SMILES: CC(=O)O.ONC(=N)NCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H14N4O3.C2H4O2/c7-4(5(11)12)2-1-3-9-6(8)10-13;1-2(3)4/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10);1H3,(H,3,4)/t4-;/m0./s1
• InChIKey: VYMCYRPQICLHKC-WCCKRBBISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(3-hydroxycarbamimidamido)pentanoic acid; acetic acid; (2S)-2-amino-5-(1-hydroxycarbamimidamido)pentanoic acid; acetic acid
• IUPAC Traditional name: (2S)-2-amino-5-(3-hydroxycarbamimidamido)pentanoic acid; acetic acid; N-ω-hydroxy-L-arginine; acetic acid
• Synonyms: NOHA acetate salt; NG-Hydroxy-L-arginine acetate salt; N^G-HYDROXY-L-ARGININE ACETATE SALT

Database IDs

• CAS Number: 53054-07-2; 53598-01-9
• MDL Number: MFCD00216150
• PubChem SID: 162092541; 24278471
• PubChem CID: 11957565

CALCULATED PROPERTIES

• Acid pKa: 2.1966505
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -6.004631
• LogD (pH = 7.4): -4.778636
• Log P: -3.2532802
• Molar Refractivity: 66.1805 cm^3
• Polarizability: 17.59352 Å^3
• Polar Surface Area: 131.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 2-8°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

DETAILS

MP Biomedicals - 02193661

Intermediate in the conversion of L-arginine into nitric oxide (NO) and citrulline.

Sigma Aldrich - H7278

Biochem/physiol Actions
Intermediate in the conversion of arginine to NO and citrulline by NO synthase.1,2,3