(2S)-2-amino-5-(3-aminocarbamimidamido)pentanoic acid; 8-hydroxy-5,7-dinitronaphthalene-2-sulfonic acid

• ChemBase ID: 156749
• Molecular Formular: C16H21N7O10S
• Molecular Mass: 503.44384
• Monoisotopic Mass: 503.10706091
• SMILES: c1cc2c(cc1S(=O)(=O)O)c(c(cc2[N+](=O)[O-])[N+](=O)[O-])O.C(C[C@@H](C(=O)O)N)CNC(=N)NN
• Canonical SMILES: [O-][N+](=O)c1cc([N+](=O)[O-])c2c(c1O)cc(cc2)S(=O)(=O)O.NNC(=N)NCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C10H6N2O8S.C6H15N5O2/c13-10-7-3-5(21(18,19)20)1-2-6(7)8(11(14)15)4-9(10)12(16)17;7-4(5(12)13)2-1-3-10-6(8)11-9/h1-4,13H,(H,18,19,20);4H,1-3,7,9H2,(H,12,13)(H3,8,10,11)/t;4-/m.0/s1
• InChIKey: FRHDIRGJHYOUQU-VWMHFEHESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(3-aminocarbamimidamido)pentanoic acid; 8-hydroxy-5,7-dinitronaphthalene-2-sulfonic acid
• IUPAC Traditional name: (2S)-2-amino-5-(3-aminocarbamimidamido)pentanoic acid; naphthol yellow S
• Synonyms: Nγ-Amino-L-arginine 2,4-dinitro-1-naphthol-7-sulfonate salt; Nω-Amino-L-arginine 2,4-dinitro-1-naphthol-7-sulfonate salt

Database IDs

• CAS Number: 137361-06-9
• MDL Number: MFCD00236796
• PubChem SID: 162250886; 24845974
• PubChem CID: 16211107

CALCULATED PROPERTIES

• Acid pKa: -2.865431
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.2185657
• LogD (pH = 7.4): -2.552657
• Log P: 1.7200323
• Molar Refractivity: 69.761 cm^3
• Polarizability: 27.038925 Å^3
• Polar Surface Area: 166.24 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C6H15N5O2 · C10H6N2O8S

DETAILS

Sigma Aldrich - 06804

Biochem/physiol Actions
Inactivates all isoforms of nitric oxide synthase1. The mechanism of NOS inactivation is not well understood, but is believed to affect only enzyme molecules that are actively metabolizing. One study of inactivation of the neuronal isoform (nNOS)2 implicated a covalent modification of the heme prosthetic group and a heme irreversibly bound to the protein.