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Identification
YMDB IDYMDB00052
NameArgininosuccinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionArgininosuccinic acid, also known as L-argininosuccinate, 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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0007-0921100000-638b5887a29712423afdJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-8790000000-bc8aa39ecc71a1589298JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0006-4101900000-c606d87ec7ffb8ef2cfaJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0090000000-27e7b2225bca7ed0bfefJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-0390000000-b66871354ad66743ff5fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-001i-1910000000-777b6f2263b573f38bcaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-3900000000-26d6466903550c40fde6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001r-8900000000-4e5455a5af85574ac9dfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0090000000-79b7ca9043632dc877e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-0590000000-8fb4f4625f241d387e92JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-06di-3910000000-55530a4477a3fde8c1c1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00di-9200000000-413c3029964c0386047aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-00di-9000000000-6ffc3b2b5da5f69de80bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-060r-0950000000-129ee81e1370707d975dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0910000000-62431d9967ced6c96b28JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-1980000000-27b5f442d411115ebaabJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-1900000000-b57bcbf0c07e921767afJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-3900000000-1fce5114c61349fc9065JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-014i-0900000000-25c094a4a18cfe463b6bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-9200000000-e518e242f12e95bbddf9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-00di-9000000000-932dfd009a8e5c41ec38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0090000000-27e7b2225bca7ed0bfefJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dj-0190000000-8ba86e35661de03d1049JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0092-2890000000-966d24fb4f820888318eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4900000000-5200a801423dd1a4b7a6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ds-0290000000-a3397e8c303fc7e6bd83JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00e9-0940000000-a964172e915808d27899JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ac3-8900000000-d4ac87f770202453bb7aJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
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 IDNot Available
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.