Canavanine
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Identification
- Generic Name
- Canavanine
- DrugBank Accession Number
- DB01833
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 176.1738
Monoisotopic: 176.09094027 - Chemical Formula
- C5H12N4O3
- Synonyms
- (L)-Canavanine
- 2-Amino-4-(guanidinooxy)butyric acid
- Canavanin
- L-Canavanine
- O-((Aminoiminomethyl)amino)-L-homoserine
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNitric oxide synthase, endothelial Not Available Humans - 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
- Fatty acids and conjugates / Guanidines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboxylic acid / Fatty acid / Guanidine / Hydrocarbon derivative / L-alpha-amino acid / Monocarboxylic acid or derivatives
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- non-proteinogenic L-alpha-amino acid (CHEBI:609827)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 3HZV514J4B
- CAS number
- 543-38-4
- InChI Key
- FSBIGDSBMBYOPN-VKHMYHEASA-N
- InChI
- InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1
- IUPAC Name
- (2S)-2-amino-4-(carbamimidamidooxy)butanoic acid
- SMILES
- N[C@@H](CCONC(N)=N)C(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0002706
- KEGG Compound
- C00308
- PubChem Compound
- 439202
- PubChem Substance
- 46507101
- ChemSpider
- 388342
- BindingDB
- 50370459
- ChEBI
- 609827
- ChEMBL
- CHEMBL443732
- ZINC
- ZINC000003869452
- PDBe Ligand
- GGB
- Wikipedia
- Canavanine
- PDB Entries
- 3lap / 3u88 / 4m2f / 4q2x / 4y4g / 5n3k / 5rpd / 5uti / 6cba / 6nse … show 7 more
Clinical Trials
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 logP -3.7 Chemaxon pKa (Strongest Acidic) 2.1 Chemaxon pKa (Strongest Basic) 10.34 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 134.45 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 61.24 m3·mol-1 Chemaxon Polarizability 17.02 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 + 0.6949 Blood Brain Barrier + 0.776 Caco-2 permeable - 0.6707 P-glycoprotein substrate Non-substrate 0.6462 P-glycoprotein inhibitor I Non-inhibitor 0.9281 P-glycoprotein inhibitor II Non-inhibitor 0.9795 Renal organic cation transporter Non-inhibitor 0.8358 CYP450 2C9 substrate Non-substrate 0.8185 CYP450 2D6 substrate Non-substrate 0.7847 CYP450 3A4 substrate Non-substrate 0.7424 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.909 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9033 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9785 Ames test AMES toxic 0.7585 Carcinogenicity Non-carcinogens 0.9017 Biodegradation Ready biodegradable 0.7581 Rat acute toxicity 2.1576 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.947 hERG inhibition (predictor II) Non-inhibitor 0.9137
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 143.1375723 predictedDarkChem Lite v0.1.0 [M-H]- 143.0612723 predictedDarkChem Lite v0.1.0 [M-H]- 131.7595 predictedDeepCCS 1.0 (2019) [M+H]+ 144.2490723 predictedDarkChem Lite v0.1.0 [M+H]+ 144.4963723 predictedDarkChem Lite v0.1.0 [M+H]+ 135.58687 predictedDeepCCS 1.0 (2019) [M+Na]+ 143.3391723 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.5840723 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.934 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsNitric oxide synthase, endothelial
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [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]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52