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Identification
YMDB IDYMDB00012
NameAdenylsuccinic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenylsuccinic acid is a substrate of the enzyme adenylosuccinase [EC 4.3.2.2] in purine metabolism pathway.
Structure
Thumb
Synonyms
  • 6-Succino-5'-adenylate
  • 6-Succino-5'-adenylic acid
  • adenyl-Succinic acid
  • adenylosuccinate
  • adenylosuccinic acid
  • Adenylsuccinate
  • Adenylsuccinic acid
  • Aspartyl adenylate
  • Aspartyl adenylic acid
  • D-ribofuranosyl-9H-purin-6-yl) mono(dihydrogen phosphate) (ester)
  • D-ribofuranosyl)-9H-purin-6-yl]
  • N(6)-(1,2-dicarboxyethyl)-AMP
  • N6-(1,2-Dicarboxyethyl)-AMP
  • Succinyl AMP
  • Succinyladenosine 5'-monophosphate
  • Succinyladenosine monophosphorate
  • Succinyladenosine monophosphoric acid
CAS number19046-78-7
WeightAverage: 463.2934
Monoisotopic: 463.074042955
InChI KeyOFBHPPMPBOJXRT-DPXQIYNJSA-N
InChIInChI=1S/C14H18N5O11P/c20-7(21)1-5(14(24)25)18-11-8-12(16-3-15-11)19(4-17-8)13-10(23)9(22)6(30-13)2-29-31(26,27)28/h3-6,9-10,13,22-23H,1-2H2,(H,20,21)(H,24,25)(H,15,16,18)(H2,26,27,28)/t5?,6-,9-,10-,13-/m1/s1
IUPAC Name2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
Traditional IUPAC Nameadenylosuccinate
Chemical FormulaC14H18N5O11P
SMILES[H]OC(=O)C([H])([H])C([H])(N([H])C1=NC([H])=NC2=C1N=C([H])N2[C@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]1([H])O[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Aspartic acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Alpha-amino acid or derivatives
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Pyrimidine
  • Imidolactam
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • 1,2-diol
  • Secondary alcohol
  • Amino acid
  • Oxacycle
  • Azacycle
  • Secondary amine
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Organic oxide
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.38 g/LALOGPS
logP-2ALOGPS
logP-5.3ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.58ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area246.68 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity96.18 m³·mol⁻¹ChemAxon
Polarizability39.51 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
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
Purine metabolismec00230 Map00230
SMPDB Reactions
GTP + Inosinic acid + L-Aspartic acidGuanosine diphosphate + phosphate + Adenylsuccinic acid
Adenylsuccinic acidFumaric acid + Adenosine monophosphate
KEGG Reactions
GTP + Inosinic acid + L-Aspartic acidphosphate + hydron + Guanosine diphosphate + Adenylsuccinic acid
Adenylsuccinic acidAdenosine monophosphate + Fumaric acid
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
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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:Buck, Ildiko; Reese, Colin B. An unambiguous synthesis of adenylosuccinic acid and its constituent nucleoside. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1990), (11), 2937-42.
External Links:
ResourceLink
CHEBI ID15919
HMDB IDHMDB00536
Pubchem Compound ID440122
Kegg IDC03794
ChemSpider ID389122
FOODB IDFDB022101
WikipediaAdenylsuccinate
BioCyc IDNot Available

Enzymes

General function:
Involved in adenylosuccinate synthase activity
Specific function:
Plays an important role in the de novo pathway and in the salvage pathway of purine nucleotide biosynthesis. Catalyzes the first commited step in the biosynthesis of AMP from IMP
Gene Name:
ADE12
Uniprot ID:
P80210
Molecular weight:
48279.10156
Reactions
GTP + IMP + L-aspartate → GDP + phosphate + N(6)-(1,2-dicarboxyethyl)-AMP.
General function:
Involved in catalytic activity
Specific function:
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:
ADE13
Uniprot ID:
Q05911
Molecular weight:
54509.89844
Reactions
N(6)-(1,2-dicarboxyethyl)AMP → fumarate + AMP.
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate → fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.