CANAVANINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H12N4O3
Molecular Weight	176.1738
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@@H](CCONC(N)=N)C(O)=O

InChI

InChIKey=FSBIGDSBMBYOPN-VKHMYHEASA-N

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

HIDE SMILES / InChI

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nitric oxide synthase, inducible 55 Target ID: CHEMBL3464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18930653 \| https://www.ncbi.nlm.nih.gov/pubmed/18485715 \| https://www.ncbi.nlm.nih.gov/pubmed/15993059	Inhibitor 8504		60.0 µM [IC50]

PubMed

Title	Date	PubMed
Glibenclamide attenuates the antiarrhythmic effect of endotoxin with a mechanism not involving K(ATP) channels.	2007-02	17064967
Proton affinity of canavanine and canaline, oxyanalogues of arginine and ornithine, from the extended kinetic method.	2006-10-12	17020263
Effects of dexamethasone and L-canavanine on the intracellular calcium-contraction relation of the rat tail artery during septic shock.	2006-09	16603690
Tight linkage between translation and MHC class I peptide ligand generation implies specialized antigen processing for defective ribosomal products.	2006-07-01	16785518
Role of non-protein amino acid L-canavanine in autoimmunity.	2006-07	16890899
High-resolution mutation mapping reveals parallel experimental evolution in yeast.	2006-07	16856782
Detrimental effects of nitric oxide inhibition on hepatic encephalopathy in rats with thioacetamide-induced fulminant hepatic failure: role of nitric oxide synthase isoforms.	2006-07	16824075
A synthetic defect in protein degradation caused by loss of Ufd4 and Rad23.	2006-03-10	16430867
Control by sugar of Saccharomyces cerevisiae flocculation for industrial ethanol production.	2006-03	16487349
Immunological and physical comparison of monomeric and dimeric phosphagen kinases: Some evolutionary implications.	2006-03	16386374
Genomewide screen reveals a wide regulatory network for di/tripeptide utilization in Saccharomyces cerevisiae.	2006-03	16361226
Ebs1p, a negative regulator of gene expression controlled by the Upf proteins in the yeast Saccharomyces cerevisiae.	2006-02	16467471
Fission yeast Dss1 associates with the proteasome and is required for efficient ubiquitin-dependent proteolysis.	2006-01-01	16149916
[Urinary enzymes as markers of functional state of kidneys with diabetic lesions].	2006	16553303
L-canavanine is a time-controlled mechanism-based inhibitor of Pseudomonas aeruginosa arginine deiminase.	2005-11-30	16305225
Identification of novel single amino acid changes that result in hyperactivation of the unique GTPase, Rheb, in fission yeast.	2005-11	16262791
Urea cycle of Fasciola gigantica: purification and characterization of arginase.	2005-11	16125991
Pas1, a G1 cyclin, regulates amino acid uptake and rescues a delay in G1 arrest in Tsc1 and Tsc2 mutants in Schizosaccharomyces pombe.	2005-10-01	16115814
L-arginine analogs as alternate substrates for nitric oxide synthase.	2005-09-01	15993059
Renal blood flow in sepsis.	2005-08	16137349
Arabidopsis ubiquitin-specific protease 6 (AtUBP6) interacts with calmodulin.	2005-07-18	15987637
Genome-wide screening for genes whose deletions confer sensitivity to mutagenic purine base analogs in yeast.	2005-06-02	15932646
Antigens from Ascaris suum trigger in vitro macrophage NO production.	2005-06	16048643
African herbal medicines in the treatment of HIV: Hypoxis and Sutherlandia. An overview of evidence and pharmacology.	2005-05-31	15927053
Lung-migrating digenean parasites: in vitro influence on nitric oxide production from normal rat pulmonary macrophages.	2005-03	15713448
Improved production of isoamyl acetate by a sake yeast mutant resistant to an isoprenoid analog and its dependence on alcohol acetyltransferase activity, but not on isoamyl alcohol production.	2005-02	16233768
Upf1p, a highly conserved protein required for nonsense-mediated mRNA decay, interacts with the nuclear pore proteins Nup100p and Nup116p.	2005-01-31	15716093
Purification, properties and alternate substrate specificities of arginase from two different sources: Vigna catjang cotyledon and buffalo liver.	2005	16094464
Derivation of genetic interaction networks from quantitative phenotype data.	2005	15833125
The mechanism and modes of inhibition of arginine kinase from the cockroach (Periplaneta americana).	2004-12	15540275
Multiple ubiquitin-specific protease genes are involved in degradation of yeast tryptophan permease Tat2 at high pressure.	2004-10-01	15451116
Inhibition of proteasome activity sensitizes dopamine neurons to protein alterations and oxidative stress.	2004-10	15480836
In vitro culture studies of Sutherlandia frutescens on human tumor cell lines.	2004-07	15182898
Comparative effects of vasopressin, norepinephrine, and L-canavanine, a selective inhibitor of inducible nitric oxide synthase, in endotoxic shock.	2004-07	14988074
Rad23 and Rpn10 serve as alternative ubiquitin receptors for the proteasome.	2004-06-25	15117949
Saccharomyces cerevisiae RAD27 complements its Escherichia coli homolog in damage repair but not mutation avoidance.	2004-06	15329499
Effect of D-arginine on antinociception induced by kyotorphin, Tyr-cav, L-cav and Tyr(Cl2)-cav in rats.	2004-06	15319811
Peroxiredoxin-null yeast cells are hypersensitive to oxidative stress and are genomically unstable.	2004-05-28	15051715
The Ubx2 and Ubx3 cofactors direct Cdc48 activity to proteolytic and nonproteolytic ubiquitin-dependent processes.	2004-05-04	15120077
Tsc1+ and tsc2+ regulate arginine uptake and metabolism in Schizosaccharomyces pombe.	2004-03-26	14718525
Effects of lipopolysaccharide on epithelium-dependent relaxation in coaxial bioassay.	2004-03-08	15033396
Effects of nitric oxide synthase inhibitors on retrograde bile salt-induced pancreatitis rats.	2004-01	15077884
Simplified qualitative method for canavanine in seeds and sprouts.	2004-01	14717378
Mutation induction in haploid yeast after split-dose radiation exposure. II. Combination of UV-irradiation and X-rays.	2004	14743343
Spectrophotometric and steady-state kinetic analysis of the biosynthetic arginine decarboxylase of Yersinia pestis utilizing arginine analogues as inhibitors and alternative substrates.	2003-12-30	14690429
Fission yeast Uve1 and Apn2 function in distinct oxidative damage repair pathways in vivo.	2003-11-21	14599746
Nitroarginine methyl ester and canavanine lower intracellular reduced glutathione.	2003-11-15	14607520
The mechanism of L-canavanine cytotoxicity: arginyl tRNA synthetase as a novel target for anticancer drug discovery.	2003-10	14692504
[Effect of extrusion on the activity of anti-nutritional factors and in vitro digestibility of protein and starch in flours of Canavalia ensiformis].	2003-09	14694814
L-canavanine inhibits L-arginine uptake by broiler chicken intestinal brush border membrane vesicles.	2003-09	14584853

Name

Type

Language

CANAVANINE

Systematic Name

English

BUTYRIC ACID, 2-AMINO-4-(GUANIDINOOXY)-, L-

Preferred Name

English

CANAVANIN

Systematic Name

English

2-AMINO-4-(GUANIDINOOXY)BUTYRIC ACID

Systematic Name

English

CANAVANINE, (+)-

Systematic Name

English

CAV

Common Name

English

L-CAV

Common Name

English

L-HOMOSERINE, O-((AMINOIMINOMETHYL)AMINO)-

Systematic Name

English

O-((AMINOIMINOMETHYL)AMINO)-L-HOMOSERINE

Systematic Name

English

CANAVANINE [HSDB]

Common Name

English

(+)-CANAVANINE

Systematic Name

English

CANAVANINE [MI]

Common Name

English

L-CANAVANINE

Systematic Name

English

Code System Code Type Description

CAS

543-38-4