Nitroarginine
Star0
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Nitroarginine
- DrugBank Accession Number
- DB04223
- Background
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)
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
- Weight
- Average: 219.1985
Monoisotopic: 219.096753929 - Chemical Formula
- C6H13N5O4
- Synonyms
- L-NNA
- N(gamma)-nitro-L-arginine
- Ngamma-Nitro-L-arginine
- omega-Nitroarginine
- External IDs
- NSC-53662
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ANitric oxide synthase 1 inhibitorHumans ANitric oxide synthase 3 inhibitorHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic acyclic compound / Allyl-type 1,3-dipolar organic compound / Amine / Amino acid / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Fatty acyl / Guanidine 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)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 7O8V7H6P2J
- CAS number
- 2149-70-4
- 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-(N'-nitrocarbamimidamido)pentanoic acid
- SMILES
- N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(O)=O
References
- General References
- Not Available
- External Links
- KEGG Compound
- C03417
- PubChem Compound
- 440005
- PubChem Substance
- 46508354
- ChemSpider
- 389023
- BindingDB
- 50225106
- ChEBI
- 27960
- ChEMBL
- CHEMBL227744
- ZINC
- ZINC000019796052
- PDBe Ligand
- NRG
- Wikipedia
- Nitroarginine
- PDB Entries
- 1ed5 / 1k2r / 3idm / 4uqr / 8nse
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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
Property Value Source Water Solubility 0.874 mg/mL ALOGPS logP -2.8 ALOGPS logP -3.8 Chemaxon logS -2.4 ALOGPS pKa (Strongest Acidic) 1.9 Chemaxon pKa (Strongest Basic) 9.22 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 154.37 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 59.91 m3·mol-1 Chemaxon Polarizability 20.19 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8729 Blood Brain Barrier + 0.5504 Caco-2 permeable - 0.6463 P-glycoprotein substrate Non-substrate 0.5623 P-glycoprotein inhibitor I Non-inhibitor 0.9627 P-glycoprotein inhibitor II Non-inhibitor 0.9694 Renal organic cation transporter Non-inhibitor 0.9008 CYP450 2C9 substrate Non-substrate 0.8412 CYP450 2D6 substrate Non-substrate 0.8015 CYP450 3A4 substrate Non-substrate 0.7115 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9308 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.897 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9946 Ames test AMES toxic 0.8475 Carcinogenicity Non-carcinogens 0.7987 Biodegradation Ready biodegradable 0.8664 Rat acute toxicity 2.3722 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8183 hERG inhibition (predictor II) Non-inhibitor 0.9218
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-9300000000-95f7951b9081bdfa98f6 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 156.9670803 predictedDarkChem Lite v0.1.0 [M-H]- 149.23561 predictedDeepCCS 1.0 (2019) [M+H]+ 157.0616803 predictedDarkChem Lite v0.1.0 [M+H]+ 151.48006 predictedDeepCCS 1.0 (2019) [M+Na]+ 156.7704803 predictedDarkChem Lite v0.1.0 [M+Na]+ 157.5732 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. DetailsNitric oxide synthase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General 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. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR
- Specific Function
- arginine binding
- Gene Name
- NOS1
- Uniprot ID
- P29475
- Uniprot Name
- Nitric oxide synthase 1
- Molecular Weight
- 160969.095 Da
References
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsNitric oxide synthase 3
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway (PubMed:1378832). NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets
- Specific Function
- actin monomer binding
- Gene Name
- NOS3
- Uniprot ID
- P29474
- Uniprot Name
- Nitric oxide synthase 3
- Molecular Weight
- 133273.59 Da
References
- 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. [Article]
- 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. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22