You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2009-04-06 16:20:51 UTC
Update Date2016-02-11 01:23:50 UTC
HMDB IDHMDB12197
Secondary Accession NumbersNone
Metabolite Identification
Common NameCanavaninosuccinate
DescriptionCanavaninosuccinate is formed from ureidohomoserine and aspartate by a human or bovine liver extract that had high argininosuccinate synthetase (EC 6.3.4.5) activity, and the subsequent formation of guanidinosuccinate is done by reductive cleavage. In the presence of ATP the optimum pH for the synthetic reaction is 8.4. This reaction can be carried out in either a tris(hydroxymethyl)aminomethane or borate buffer. Subsequent addition of dithiothreitol in the presence of Fe2+ resulted in the cleavage of some of the synthesized canavaninosuccinate to form guanidinosuccinate and homoserine. Synthesis of canavaninosuccinate was strongly inhibited by added argininosuccinate, less so by canavaninosuccinate, arginine, canavanine, glycine, or 2,3-dimercaptopropanol. All the reactions, starting with canavaninosuccinate and down to the formation of guanidinoacetate and guanidinosuccinate have been demonstrated in human tissue ( (PMID: 241511 ).
Structure
Thumb
Synonyms
ValueSource
Canavaninosuccinic acidHMDB
Chemical FormulaC9H16N4O7
Average Molecular Weight292.2459
Monoisotopic Molecular Weight292.101898886
IUPAC Name2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid
Traditional Name2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid
CAS Registry Number56073-32-6
SMILES
NC(CCONC(=N)NC(CC(O)=O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C9H16N4O7/c10-4(7(16)17)1-2-20-13-9(11)12-5(8(18)19)3-6(14)15/h4-5H,1-3,10H2,(H,14,15)(H,16,17)(H,18,19)(H3,11,12,13)
InChI KeyInChIKey=SGYMGUGIGTWWLU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Tricarboxylic acid or derivatives
  • Amino fatty acid
  • Fatty acyl
  • Guanidine
  • Carboximidamide
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.62 mg/mLALOGPS
logP-3.3ALOGPS
logP-6.1ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)10.33ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area195.06 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity82.63 m3·mol-1ChemAxon
Polarizability26.74 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNot Available details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB028845
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCANAVANINOSUCCINATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12197
Metagene LinkHMDB12197
METLIN IDNot Available
PubChem Compound25201068
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Koller A, Aldwin L, Natelson S: Hepatic synthesis of canavaninosuccinate from ureidohomoserine and aspartate, and its conversion to guanidinosuccinate. Clin Chem. 1975 Nov;21(12):1777-82. [241511 ]

Enzymes

General function:
Involved in argininosuccinate synthase activity
Specific function:
Not Available
Gene Name:
ASS1
Uniprot ID:
P00966
Molecular weight:
46530.055
General function:
Involved in argininosuccinate lyase activity
Specific function:
Not Available
Gene Name:
ASL
Uniprot ID:
P04424
Molecular weight:
51657.505