Nitroarginine

Identification

Name
Nitroarginine
Accession Number
DB04223  (EXPT02387)
Type
Small Molecule
Groups
Experimental, Investigational
Description

An inhibitor of nitric oxide synthetase which has been shown to prevent glutamate toxicity. Nitroarginine has been experimentally tested for its ability to prevent ammonia toxicity and ammonia-induced alterations in brain energy and ammonia metabolites. (Neurochem Res 1995:200(4):451-6)

Structure
Thumb
Synonyms
  • L-NNA
  • N-nitro-l-arginine
  • N-omega-nitro-l-arginine
  • N(g)-nitro-l-arginine
  • N(g)-nitroarginine
  • N5-(Nitroamidino)-L-2,5-diaminopentanoic acid
  • NG-nitro-l-arginine
  • NG-NO2-L-Arg
  • Ngamma-nitro-l-arginine
  • Nitro-l-arginine
  • Nomega-nitro-l-arginine
  • NRG
External IDs
NSC-53662
Categories
UNII
7O8V7H6P2J
CAS number
2149-70-4
Weight
Average: 219.1985
Monoisotopic: 219.096753929
Chemical Formula
C6H13N5O4
InChI Key
MRAUNPAHJZDYCK-BYPYZUCNSA-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
IUPAC Name
(2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoic acid
SMILES
N[[email protected]@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot AvailableHuman
UNitric oxide synthase, brainNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C03417
PubChem Compound
440005
PubChem Substance
46508354
ChemSpider
389023
BindingDB
50225106
ChEMBL
CHEMBL227744
HET
NRG
PDB Entries
1ed5 / 1k2r / 3idm / 4uqr / 8nse

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.874 mg/mLALOGPS
logP-2.8ALOGPS
logP-3.4ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)9.16ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area157.05 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.91 m3·mol-1ChemAxon
Polarizability20.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8729
Blood Brain Barrier+0.5504
Caco-2 permeable-0.6463
P-glycoprotein substrateNon-substrate0.5623
P-glycoprotein inhibitor INon-inhibitor0.9627
P-glycoprotein inhibitor IINon-inhibitor0.9694
Renal organic cation transporterNon-inhibitor0.9008
CYP450 2C9 substrateNon-substrate0.8412
CYP450 2D6 substrateNon-substrate0.8015
CYP450 3A4 substrateNon-substrate0.7115
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9308
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.897
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9946
Ames testAMES toxic0.8475
CarcinogenicityNon-carcinogens0.7987
BiodegradationReady biodegradable0.8664
Rat acute toxicity2.3722 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8183
hERG inhibition (predictor II)Non-inhibitor0.9218
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Nitro fatty acids / Nitroguanidines / Nitramines / Amino acids / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic zwitterions
show 4 more
Substituents
L-alpha-amino acid / Nitro fatty acid / Nitroguanidine / Fatty acid / Fatty acyl / Nitramine / Guanidine / Amino acid / Organic nitro compound / Carboxylic acid
show 18 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
guanidines, non-proteinogenic L-alpha-amino acid, L-arginine derivative, N-nitro compound (CHEBI:27960)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
Gene Name
NOS3
Uniprot ID
P29474
Uniprot Name
Nitric oxide synthase, endothelial
Molecular Weight
133287.62 Da
References
  1. Raman CS, Li H, Martasek P, Southan G, Masters BS, Poulos TL: Crystal structure of nitric oxide synthase bound to nitro indazole reveals a novel inactivation mechanism. Biochemistry. 2001 Nov 13;40(45):13448-55. [PubMed:11695891]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. P...
Gene Name
NOS1
Uniprot ID
P29475
Uniprot Name
Nitric oxide synthase, brain
Molecular Weight
160969.095 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:25