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

Molecular Formula	C5H12N4O3
Molecular Weight	176.1738
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nitric oxide synthase, inducible 50 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 8297		60.0 µM [IC50]

PubMed

Title	Date	PubMed
Spectrophotometric and steady-state kinetic analysis of the biosynthetic arginine decarboxylase of Yersinia pestis utilizing arginine analogues as inhibitors and alternative substrates.	2003 Dec 30	14690429
Nitroarginine methyl ester and canavanine lower intracellular reduced glutathione.	2003 Nov 15	14607520
Fission yeast Uve1 and Apn2 function in distinct oxidative damage repair pathways in vivo.	2003 Nov 21	14599746
The mechanism of L-canavanine cytotoxicity: arginyl tRNA synthetase as a novel target for anticancer drug discovery.	2003 Oct	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 Sep	14694814
L-canavanine inhibits L-arginine uptake by broiler chicken intestinal brush border membrane vesicles.	2003 Sep	14584853
Mutation induction in haploid yeast after split-dose radiation exposure. II. Combination of UV-irradiation and X-rays.	2004	14743343
The mechanism and modes of inhibition of arginine kinase from the cockroach (Periplaneta americana).	2004 Dec	15540275
Effects of nitric oxide synthase inhibitors on retrograde bile salt-induced pancreatitis rats.	2004 Jan	15077884
Simplified qualitative method for canavanine in seeds and sprouts.	2004 Jan	14717378
In vitro culture studies of Sutherlandia frutescens on human tumor cell lines.	2004 Jul	15182898
Comparative effects of vasopressin, norepinephrine, and L-canavanine, a selective inhibitor of inducible nitric oxide synthase, in endotoxic shock.	2004 Jul	14988074
Saccharomyces cerevisiae RAD27 complements its Escherichia coli homolog in damage repair but not mutation avoidance.	2004 Jun	15329499
Effect of D-arginine on antinociception induced by kyotorphin, Tyr-cav, L-cav and Tyr(Cl2)-cav in rats.	2004 Jun	15319811
Rad23 and Rpn10 serve as alternative ubiquitin receptors for the proteasome.	2004 Jun 25	15117949
Tsc1+ and tsc2+ regulate arginine uptake and metabolism in Schizosaccharomyces pombe.	2004 Mar 26	14718525
Effects of lipopolysaccharide on epithelium-dependent relaxation in coaxial bioassay.	2004 Mar 8	15033396
Peroxiredoxin-null yeast cells are hypersensitive to oxidative stress and are genomically unstable.	2004 May 28	15051715
The Ubx2 and Ubx3 cofactors direct Cdc48 activity to proteolytic and nonproteolytic ubiquitin-dependent processes.	2004 May 4	15120077
Inhibition of proteasome activity sensitizes dopamine neurons to protein alterations and oxidative stress.	2004 Oct	15480836
Multiple ubiquitin-specific protease genes are involved in degradation of yeast tryptophan permease Tat2 at high pressure.	2004 Oct 1	15451116
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
Renal blood flow in sepsis.	2005 Aug	16137349
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 Feb	16233768
Upf1p, a highly conserved protein required for nonsense-mediated mRNA decay, interacts with the nuclear pore proteins Nup100p and Nup116p.	2005 Jan 31	15716093
Arabidopsis ubiquitin-specific protease 6 (AtUBP6) interacts with calmodulin.	2005 Jul 18	15987637
Antigens from Ascaris suum trigger in vitro macrophage NO production.	2005 Jun	16048643
Genome-wide screening for genes whose deletions confer sensitivity to mutagenic purine base analogs in yeast.	2005 Jun 2	15932646
Lung-migrating digenean parasites: in vitro influence on nitric oxide production from normal rat pulmonary macrophages.	2005 Mar	15713448
African herbal medicines in the treatment of HIV: Hypoxis and Sutherlandia. An overview of evidence and pharmacology.	2005 May 31	15927053
Identification of novel single amino acid changes that result in hyperactivation of the unique GTPase, Rheb, in fission yeast.	2005 Nov	16262791
Urea cycle of Fasciola gigantica: purification and characterization of arginase.	2005 Nov	16125991
L-canavanine is a time-controlled mechanism-based inhibitor of Pseudomonas aeruginosa arginine deiminase.	2005 Nov 30	16305225
Pas1, a G1 cyclin, regulates amino acid uptake and rescues a delay in G1 arrest in Tsc1 and Tsc2 mutants in Schizosaccharomyces pombe.	2005 Oct 1	16115814
L-arginine analogs as alternate substrates for nitric oxide synthase.	2005 Sep 1	15993059
[Urinary enzymes as markers of functional state of kidneys with diabetic lesions].	2006	16553303
Ebs1p, a negative regulator of gene expression controlled by the Upf proteins in the yeast Saccharomyces cerevisiae.	2006 Feb	16467471
Fission yeast Dss1 associates with the proteasome and is required for efficient ubiquitin-dependent proteolysis.	2006 Jan 1	16149916
Role of non-protein amino acid L-canavanine in autoimmunity.	2006 Jul	16890899
High-resolution mutation mapping reveals parallel experimental evolution in yeast.	2006 Jul	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 Jul	16824075
Tight linkage between translation and MHC class I peptide ligand generation implies specialized antigen processing for defective ribosomal products.	2006 Jul 1	16785518
Control by sugar of Saccharomyces cerevisiae flocculation for industrial ethanol production.	2006 Mar	16487349
Immunological and physical comparison of monomeric and dimeric phosphagen kinases: Some evolutionary implications.	2006 Mar	16386374
Genomewide screen reveals a wide regulatory network for di/tripeptide utilization in Saccharomyces cerevisiae.	2006 Mar	16361226
A synthetic defect in protein degradation caused by loss of Ufd4 and Rad23.	2006 Mar 10	16430867
Proton affinity of canavanine and canaline, oxyanalogues of arginine and ornithine, from the extended kinetic method.	2006 Oct 12	17020263
Effects of dexamethasone and L-canavanine on the intracellular calcium-contraction relation of the rat tail artery during septic shock.	2006 Sep	16603690
Glibenclamide attenuates the antiarrhythmic effect of endotoxin with a mechanism not involving K(ATP) channels.	2007 Feb	17064967

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:39:43 GMT 2023` Edited by `admin` on `Fri Dec 15 20:39:43 GMT 2023`
Record UNII	3HZV514J4B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CANAVANINE

Systematic Name

English

CANAVANIN

Systematic Name

English

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

Common 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