Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2018-05-28 22:35:34 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
Synonyms
SynonymSource
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoateChEBI
L-CanavanineChEBI
2-Amino-4-(guanidinooxy)butyric acidKegg
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoic acidGenerator
2-Amino-4-(guanidinooxy)butyrateGenerator
CanavaninHMDB
O-((Aminoiminomethyl)amino)homoserineHMDB
CanavanineMeSH
(l)-canavaninebiospider
543-38-4 (FREE BASE)biospider
Butyric acid, 2-amino-4-(guanidinooxy)-, Lbiospider
Butyric acid, 2-amino-4-(guanidinooxy)-, L-biospider
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 Solubility2.77 g/LALOGPS
logP-3.9ALOGPS
logP-3.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.1ChemAxon
pKa (Strongest Basic)10.34ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area134.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity61.24 m³·mol⁻¹ChemAxon
Polarizability17.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC5H12N4O3
IUPAC name(2S)-2-amino-4-(carbamimidamidooxy)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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0uk9-2930000000-f0b7791e84a9692c9896View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0uk9-2930000000-f0b7791e84a9692c9896View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-97acb154cb1e58dea04aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9310000000-65f69dfa455b1707a1e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-1bb8236fdf1b58516604View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-01b9-4900000000-bb3b6e4a69d652b8ca9fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-06di-9400000000-d5093b67a7ae4861da94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9100000000-c152969360d44d895d0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0k96-9000000000-277b39712e9095e29987View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-004i-0900000000-ba76dc7ddbe1f642142aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004i-7900000000-e4399ab6ff268986734eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00b9-9100000000-fa6508b89d97cec98552View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-05di-9000000000-3dadb3257235bbed4b41View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0ab9-9000000000-c1e347b18ad0b5e0667eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-1bb8236fdf1b58516604View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01b9-4900000000-6273e4c764e53645e523View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-06di-9400000000-d5093b67a7ae4861da94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9100000000-c152969360d44d895d0fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0k96-9000000000-277b39712e9095e29987View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0900000000-ba76dc7ddbe1f642142aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-7900000000-e4399ab6ff268986734eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00b9-9100000000-e6d11248bff03dbe3f4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-05di-9000000000-444161e8e39f43477d96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kcr-3900000000-3035f2c40483995fefeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9500000000-87a602f996e2b691bc56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-231b107110171e252832View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-3900000000-83f24d50a43c98428bd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-71a411b47be6341daaf5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c459abc57107fc6f4bf1View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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
allelochemicDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti feedantDUKE
anti flu22587 A substance that destroys or inhibits replication of viruses.DUKE
anti metabolicDUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
juvabionalDUKE
lupus generating52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
mitogenicDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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).