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Identification
YMDB IDYMDB00593
Name(N(omega)-L-arginino)succinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(N(omega)-L-arginino)succinic acid, also known as N-(L-arginino) succinate, 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 (N(omega)-L-arginino)succinic acid is a very strong basic compound (based on its pKa) (N(omega)-L-arginino)succinic acid exists in both E. coli (prokaryote) and yeast (eukaryote).
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-(Nomega-L-Arginino)succinate
  • 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-(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(omega)-(L-arginino)succinate
  • N(omega)-(L-arginino)succinic acid
  • 2-(Nomega-L-arginino)succinic acid
  • (N(Omega)-L-arginino)succinate
CAS number2387-71-5
WeightAverage: 290.2731
Monoisotopic: 290.122634328
InChI KeyKDZOASGQNOPSCU-ZBHICJROSA-N
InChIInChI=1S/C10H18N4O6/c11-5(8(17)18)2-1-3-13-10(12)14-6(9(19)20)4-7(15)16/h5-6H,1-4,11H2,(H,15,16)(H,17,18)(H,19,20)(H3,12,13,14)/t5-,6?/m0/s1
IUPAC Name2-{3-[(4S)-4-amino-4-carboxybutyl]carbamimidamido}butanedioic acid
Traditional IUPAC Namearginosuccinate
Chemical FormulaC10H18N4O6
SMILESN[C@@H](CCCNC(=N)NC(CC(O)=O)C(O)=O)C(O)=O
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
Polarizability27.52 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 ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15682
HMDB IDHMDB00052
Pubchem Compound ID16950
Kegg IDC03406
ChemSpider ID389016
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.