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Showing Compound L-Canavanine (FDB000505)

Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2019-11-26 02:54:54 UTC
Primary IDFDB000505
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Canavanine
DescriptionStored in large quantities in the seeds of leguminous plants in three subfamilies. Isol. originally from Jackbean (Canavalia ensiformis) L-(+)-(S)-Canavanine is a non-proteinogenic amino acid of certain leguminous plants. It is structurally related to the proteinogenic amino acid, L-arginine. Canavanine is accumulated primarily in the seeds where it serves both as a defensive compound against herbivores and a vital source of nitrogen for the growing embryo. Organisms that consume it can mistakenly incorporate it into their own proteins in the place of arginine, thereby producing structurally aberrant proteins that may not function properly. Some specialized herbivores tolerate L-canavanine either because they metabolize it efficiently or avoid its incorporation into their own nascent proteins.; L-Canavanine, a non-protein amino acid of certain leguminous plants, is related structurally to the protein amino acid, L-arginine. Canavanine is accumulated primarily in the seeds where it serves both as a defensive compound against herbivores and a vital source of nitrogen for the growing embryo. Organisms that consume it can mistakenly incorporate it into their own proteins, in the place of arginine thereby producing structurally aberrant proteins that may not function properly or not at all. Some specialized herbivores tolerate L-canavanine either because they metabolize it efficiently or avoid its incorporation into their own nascent proteins. -- Wikipedia (unverified). L-Canavanine is found in many foods, some of which are mamey sapote, purslane, hard wheat, and cabbage.
CAS Number543-38-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoateChEBI
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoic acidGenerator
(l)-canavaninebiospider
2-Amino-4-(guanidinooxy)butyric acidbiospider
543-38-4 (FREE BASE)biospider
Butyric acid, 2-amino-4-(guanidinooxy)-, Lbiospider
Butyric acid, 2-amino-4-(guanidinooxy)-, L-biospider
Canavaninbiospider
Canavaninebiospider
Canavanine; L-formdb_source
GGBbiospider
L-2-AMINO-4-(GUANIDINOOXY)BUTYRIC ACIDbiospider
L-canavaninebiospider
L-canavanine sulfatebiospider
L-homoserine, o-((aminoiminomethyl)amino)-biospider
L-Homoserine, O-((aminoiminomethyl)amino)- (9CI)biospider
L(+)-canavaninebiospider
NSC8921 (SULFATE)biospider
O-((aminoiminomethyl)amino)-l-homoserinebiospider
O-((aminoiminomethyl)amino)homoserinebiospider
Predicted Properties
PropertyValueSource
Water Solubility11.1 g/LALOGPS
logP-3.8ALOGPS
logP-4.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.1ChemAxon
pKa (Strongest Basic)9.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area136.95 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity40.34 m³·mol⁻¹ChemAxon
Polarizability17.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H12N4O3
IUPAC name2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid
InChI IdentifierInChI=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)
InChI KeyFSBIGDSBMBYOPN-UHFFFAOYSA-N
Isomeric SMILESNC(CCON=C(N)N)C(O)=O
Average Molecular Weight176.1738
Monoisotopic Molecular Weight176.09094027
Classification
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 34.09%; H 6.87%; N 31.80%; O 27.24%DFC
Melting PointMp 184°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-3.324
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +7.9 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0569-2900000000-6018918223cd95093d452015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06zi-9700000000-c7ea219fb6909c4603dd2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fr-9000000000-383c77609becf60558952015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-4900000000-f69af7725371043afbed2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-9400000000-a77fd65e4ff93ac42c572015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-4bc013713f2338a457af2015-05-27View Spectrum
NMRNot Available
ChemSpider ID388342
ChEMBL IDCHEMBL443732
KEGG Compound IDC00308
Pubchem Compound ID439202
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01833
HMDB IDHMDB02706
CRC / DFC (Dictionary of Food Compounds) IDHDB91-Y:BCZ27-E
EAFUS IDNot Available
Dr. Duke IDCANAVANINE
BIGG IDNot Available
KNApSAcK IDC00001347
HET IDGGB
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCanavanine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
AllelochemicA chemical released by plants that interacts with other organisms, influencing their behavior or growth. Its biological role involves plant defense and communication. Therapeutically, allelochemics have anti-inflammatory, antimicrobial, and antioxidant properties, with applications in managing anxiety, pain, and infections, as well as potential anticancer uses.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti feedantA substance that inhibits normal feeding behavior, found in certain plants, deterring insects and animals from consuming them. Its therapeutic applications include pest control, while key medical uses involve managing insect-borne diseases and reducing crop damage.DUKE
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti-metabolicA substance that interferes with normal metabolic processes by competing with or replacing essential metabolites, used therapeutically to inhibit cancer cell growth, treat infections, and manage autoimmune diseases, with key applications in chemotherapy and antibiotic development.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Herbicide24527 A chemical agent that kills or inhibits plant growth, used in agriculture to control weeds and pests. It has no direct biological role or therapeutic applications in human medicine, but its development has led to the creation of related compounds with potential medical uses, such as anticancer agents.DUKE
JuvabionalA regulator of insect development, reproduction, and growth, juvenile hormone inhibitor, used in pest control and insecticide development, with potential applications in agriculture and entomology.DUKE
Lupus generating52209 An autoantibody-inducing factor, playing a role in autoimmune disease development. Therapeutically, it has no direct application, but understanding its biological role aids in lupus diagnosis and management, with key medical uses in researching systemic lupus erythematosus (SLE) treatments and biomarkers.DUKE
MitogenicA substance that stimulates cell division, triggering mitosis, with roles in growth, development, and tissue repair. Therapeutically, mitogens are used to enhance wound healing, tissue regeneration, and in cancer treatments to stimulate immune response. Key medical uses include promoting cell growth in damaged tissues and supporting hematopoiesis.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).