GtoPdb Ligand ID: 8759

Synonyms: compound 2 [PMID: 9667974] | nitroarginine
Compound class: Synthetic organic
Comment: L-NNA is an arginine analogue used as a biochemical tool in the study of nitric oxide and its biological effects. L-NNA inhibits the endothelial and neuronal isoforms of nitric oxide synthase (NOS), eNOS and nNOS respectively more potently than the inducible iNOS [1].
Selective nNOS inhibitors are being pursued for their potential to treat neurological disorders caused by excessive production of nitric oxide.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 7
Topological polar surface area 156.87
Molecular weight 219.1
XLogP -2.55
No. Lipinski's rules broken 0
Canonical SMILES [O-][N+](=O)NC(=NCCCC(C(=O)O)N)N
Isomeric SMILES [O-][N+](=O)NC(=NCCC[C@@H](C(=O)O)N)N
InChI InChI=1S/C6H13N5O4/c7-4(5(12)13)2-1-3-9-6(8)10-11(14)15/h4H,1-3,7H2,(H,12,13)(H3,8,9,10)/t4-/m0/s1
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Neuronal NOS Hs Inhibitor Inhibition 7.8 pKi - 1
pKi 7.8 (Ki 1.5x10-8 M) [1]
Endothelial NOS Hs Inhibitor Inhibition 7.5 pKi - 1
pKi 7.5 (Ki 3x10-8 M) [1]
Inducible NOS Hs Inhibitor Inhibition 6.2 pKi - 1
pKi 6.2 (Ki 6.7x10-7 M) [1]