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
Version4.0
Creation Date2009-04-06 16:20:51 UTC
Update Date2017-09-27 08:26:55 UTC
HMDB IDHMDB0012197
Secondary Accession Numbers
  • HMDB12197
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 KeySGYMGUGIGTWWLU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as aspartic acid and derivatives. These are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Guanidine
  • Amino acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity82.63 m³·mol⁻¹ChemAxon
Polarizability26.74 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6w-7390000000-298f023d33a76d4a5920View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-6203900000-5c88f219591d48415908View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056s-2390000000-fa1aee0fffe153c2a117View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-8890000000-622e7bf062e59c220aecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pdi-8910000000-9d6217950ba3f6b7edf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-007p-1970000000-b5fd2f62bc0ab84e571eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00c0-2900000000-7f5e5ccd7e3708acbe41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0adl-9600000000-dfd0944b8c755104ffeeView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
UrineDetected but not Quantified Adult (>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
METLIN IDNot Available
PubChem Compound25201068
PDB IDNot Available
ChEBI ID89639
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. [PubMed: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