canavaninosuccinate (PAMDB120244)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120244
Identification
Name: canavaninosuccinate
Description:Canavaninosuccinate 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Canavaninosuccinic acid
Chemical Formula: C9H15N4O7
Average Molecular Weight: 291.24
Monoisotopic Molecular Weight: 294.11755
InChI Key: SGYMGUGIGTWWLU-UHFFFAOYSA-M
InChI: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)/p-1
CAS number: 56073-32-6
IUPAC Name:2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid
Traditional IUPAC Name: 2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid
SMILES:C(ONC(=[N+])NC(CC(=O)[O-])C(=O)[O-])CC(C([O-])=O)[N+]
Chemical Taxonomy
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.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Aspartic 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 Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:Not Available
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
canavaninosuccinate → L-canavanine + fumarate
O-ureidohomoserine + L-aspartate + ATP → Hydrogen ion + canavaninosuccinate + AMP + diphosphate
Pathways:
    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
    References
    References:
    • 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 ]
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    HMDBHMDB12197
    PUBCHEM25244319