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Showing Compound Argininosuccinic acid (FDB021885)

Record Information
Version1.0
Creation date2011-09-21 00:04:31 UTC
Update date2015-10-09 22:29:36 UTC
Primary IDFDB021885
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArgininosuccinic acid
DescriptionArginosuccinic acid is a basic amino acid. Some cells synthesize it from citrulline, aspartic acid and use it as a precursor for arginine in the urea cycle or Citrulline-NO cycle. The enzyme that catalyzes the reaction is argininosuccinate synthetase. Argininosuccinic acid is a precursor to fumarate in the citric acid cycle via argininosuccinate lyase. Defects in the arginosuccinate lyase enzyme can lead to arginosuccinate lyase deficiency. Argininosuccinate (ASA) lyase deficiency results in defective cleavage of ASA. This leads to an accumulation of ASA in cells and an excessive excretion of ASA in urine (arginosuccinic aciduria). In virtually all respects, this disorder shares the characteristics of other urea cycle defects. The most important characteristic of ASA lyase deficiency is its propensity to cause hyperammonemia in affected individuals. ASA in affected individuals is excreted by the kidney at a rate practically equivalent to the glomerular filtration rate (GFR). Whether ASA itself causes a degree of toxicity due to hepatocellular accumulation is unknown; such an effect could help explain hyperammonemia development in affected individuals. Regardless, the name of the disease is derived from the rapid clearance of ASA in urine, although elevated levels of ASA can be found in plasma. ASA lyase deficiency is associated with high mortality and morbidity rates. Symptoms of ASA lyase deficiency include anorexia, irritability rapid breathing, lethargy and vomiting. Extreme symptoms include coma and cerebral edema. [HMDB]
CAS Number2387-71-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
ArgininosuccinateGenerator
2-(N(omega)-L-arginine)succinatehmdb
2-(N(omega)-L-arginine)succinic acidhmdb
2-(N(omega)-L-arginino)succinatehmdb
2-(N(omega)-L-arginino)succinic acidhmdb
2-(Nomega-L-arginino)succinateKegg
2-(Nomega-L-arginino)succinic acidGenerator
2-(Nw-L-arginino)butanedioatehmdb
2-(Nw-L-arginino)butanedioic acidhmdb
Argininosuccinic acidhmdb
Arginosuccinatehmdb
Arginosuccinic acidhmdb
ASAhmdb
L-Argininosuccinatehmdb
L-Argininosuccinic acidhmdb
L-Arginosuccinatehmdb
L-Arginosuccinic acidhmdb
N-(((4-amino-4-carboxybutyl)amino)iminomethyl)-L-Aspartatehmdb
N-(((4-amino-4-carboxybutyl)amino)iminomethyl)-L-Aspartic acidhmdb
N-(L-arginino) succinatehmdb
N-(L-arginino) succinic acidhmdb
N-(L-Arginino)succinatehmdb
N-(L-Arginino)succinic acidhmdb
N-[(4-amino-4-carboxybutyl)amidino]-L-Aspartatehmdb
N-[(4-amino-4-carboxybutyl)amidino]-L-Aspartic acidhmdb
N-[[(4-amino-4-carboxybutyl)amino]iminomethyl]-L-Aspartatehmdb
N-[[(4-amino-4-carboxybutyl)amino]iminomethyl]-L-Aspartic acidhmdb
N(omega)-(L-arginino)succinatehmdb
N(omega)-(L-arginino)succinic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.89 g/LALOGPS
logP-3.4ALOGPS
logP-6.4ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.04ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area174.34 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity86.26 m³·mol⁻¹ChemAxon
Polarizability27.81 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H18N4O6
IUPAC name(2S)-2-[({2-[(4S)-4-amino-4-carboxybutyl]hydrazin-1-yl}methylidene)amino]butanedioic acid
InChI IdentifierInChI=1S/C10H18N4O6/c11-6(9(17)18)2-1-3-13-14-5-12-7(10(19)20)4-8(15)16/h5-7,13H,1-4,11H2,(H,12,14)(H,15,16)(H,17,18)(H,19,20)/t6-,7-/m0/s1
InChI KeyWSQWJAOQSDPYTD-BQBZGAKWSA-N
Isomeric SMILES[H][C@](N)(CCCNN=CN[C@@]([H])(CC(O)=O)C(O)=O)C(O)=O
Average Molecular Weight290.2731
Monoisotopic Molecular Weight290.122634328
Classification
Description Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • L-alpha-amino acid
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino acid
  • Carboxylic acid amidrazone
  • Formamidine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Amidine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSArgininosuccinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-6980000000-e1445743e09c250f995aSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-1790000000-c330aee08216318731da2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002k-3970000000-bc24f964a0e07f4a95d52016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fe0-9700000000-5881d3cd091cf6ae53352016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0012-0960000000-8e6b5385b975d46fd9d32016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-1900000000-9bbe051e6a4fe609d9ec2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9800000000-f9d9e6138e11c18a70002016-09-12View Spectrum
NMRNot Available
ChemSpider ID16059
ChEMBL IDNot Available
KEGG Compound IDC03406
Pubchem Compound ID16950
Pubchem Substance IDNot Available
ChEBI ID15682
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00052
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID41790
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArgininosuccinic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Argininosuccinate synthaseASS1P00966
Argininosuccinate lyaseASLP04424
Adenylosuccinate lyaseADSLP30566
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020 map00330
Aspartate MetabolismSMP00067 map00250
Urea CycleSMP00059 map00330
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference