Argininosuccinic acid (YMDB00052)

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
MOLSDFPDBSMILESInChI
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 acid ↔ L-Arginine + Fumaric acid
L-Aspartic acid + Adenosine triphosphate + Citrulline ↔ Adenosine 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableJSpectraViewer
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
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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 IDFDB021885
WikipediaArgininosuccinic_acid
BioCyc IDNot Available

Enzymes

Protein Details
1. Argininosuccinate synthase
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.
Protein Details
2. Argininosuccinate lyase
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.