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Identification
YMDB IDYMDB00052
NameArgininosuccinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionArgininosuccinic acid, also known as L-argininosuccinate or ASA, 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. Argininosuccinic acid is a very strong basic compound (based on its pKa). Argininosuccinic acid exists in all living species, ranging from bacteria to humans. Argininosuccinic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-(N(omega)-L-arginine)succinate
  • 2-(N(omega)-L-arginine)succinic acid
  • 2-(N(omega)-L-arginino)succinate
  • 2-(N(omega)-L-arginino)succinic acid
  • 2-(Nw-L-arginino)butanedioate
  • 2-(Nw-L-arginino)butanedioic acid
  • Argininosuccinate
  • Argininosuccinic acid
  • Arginosuccinate
  • Arginosuccinic acid
  • ASA
  • L-Argininosuccinate
  • L-Argininosuccinic acid
  • L-Arginosuccinate
  • L-Arginosuccinic acid
  • N-(((4-amino-4-carboxybutyl)amino)iminomethyl)-L-Aspartate
  • N-(((4-amino-4-carboxybutyl)amino)iminomethyl)-L-Aspartic acid
  • N-(L-arginino) succinate
  • N-(L-arginino) succinic acid
  • N-(L-Arginino)succinate
  • N-(L-Arginino)succinic acid
  • N-[(4-amino-4-carboxybutyl)amidino]-L-Aspartate
  • N-[(4-amino-4-carboxybutyl)amidino]-L-Aspartic acid
  • N-[[(4-amino-4-carboxybutyl)amino]iminomethyl]-L-Aspartate
  • N-[[(4-amino-4-carboxybutyl)amino]iminomethyl]-L-Aspartic acid
  • N(omega)-(L-arginino)succinate
  • N(omega)-(L-arginino)succinic acid
  • 2-(Nomega-L-arginino)succinate
  • 2-(Nomega-L-arginino)succinic acid
  • Acid, argininosuccinic
  • N-(4-Amino-4-carboxybutyl)amidino-L-aspartic acid
CAS number2387-71-5
WeightAverage: 290.2731
Monoisotopic: 290.122634328
InChI KeyWSQWJAOQSDPYTD-BQBZGAKWSA-N
InChIInChI=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
IUPAC Name(2S)-2-{N'-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid
Traditional IUPAC Nameargininosuccinic acid
Chemical FormulaC10H18N4O6
SMILES[H]OC(=O)C([H])([H])[C@]([H])(N([H])C([H])=NN([H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(N([H])[H])C(=O)O[H])C(=O)O[H]
Chemical Taxonomy
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
  • Alpha-amino acid
  • L-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
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.46 g/LALOGPS
logP-3.2ALOGPS
logP-5.8ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.14ChemAxon
pKa (Strongest Basic)12.39ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area185.83 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity75.31 m³·mol⁻¹ChemAxon
Polarizability27.6 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Arginine and proline metabolismec00330 Map00330
SMPDB ReactionsNot Available
KEGG Reactions
Argininosuccinic acidL-Arginine + Fumaric acid
L-Aspartic acid + Adenosine triphosphate + CitrullineAdenosine monophosphate + Pyrophosphate + Argininosuccinic acid + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Abadjieva, A., Pauwels, K., Hilven, P., Crabeel, M. (2001). "A new yeast metabolon involving at least the two first enzymes of arginine biosynthesis: acetylglutamate synthase activity requires complex formation with acetylglutamate kinase." J Biol Chem 276:42869-42880.11553611
Synthesis Reference:Hagino, Koji; Nakanishi, Toshihide. Fermentative production of L-arginosuccinic acid. Jpn. Kokai Tokkyo Koho (1980), 3 pp.
External Links:
ResourceLink
CHEBI ID15682
HMDB IDHMDB00052
Pubchem Compound ID439998
Kegg IDC03406
ChemSpider ID17215918
FOODB IDFDB021885
WikipediaArgininosuccinic_acid
BioCyc IDNot Available

Enzymes

General function:
Involved in argininosuccinate synthase activity
Specific function:
In yeast, as can have a catabolic function since it allows efficient utilization of citrulline via arginine and the reactions involved in the arginase pathway
Gene Name:
ARG1
Uniprot ID:
P22768
Molecular weight:
46939.30078
Reactions
ATP + L-citrulline + L-aspartate → AMP + diphosphate + N(omega)-(L-arginino)succinate.
General function:
Involved in argininosuccinate lyase activity
Specific function:
2-(N(omega)-L-arginino)succinate = fumarate + L-arginine
Gene Name:
ARG4
Uniprot ID:
P04076
Molecular weight:
51988.69922
Reactions
2-(N(omega)-L-arginino)succinate → fumarate + L-arginine.