Adenylsuccinic acid (PAMDB000340)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000340
Identification
Name: Adenylsuccinic acid
Description:Adenylsuccinic acid is a substrate of the enzyme adenylosuccinase (EC 4.3.2.2) in purine metabolism pathway. It is converted from IMP by adenylosuccinate synthetase (EC:6.3.4.4). In alanine, aspartate and glutamate metabolism pathway, it is converted from L-aspartate and a product of adenylosuccinate synthetase. (KEGG).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 6-Succino-5'-adenylate
  • 6-Succino-5'-adenylic acid
  • Adenyl-Succinate
  • Adenyl-Succinic acid
  • Adenylosuccinate
  • Adenylosuccinic acid
  • Adenylsuccinate
  • Adenylsuccinic acid
  • ASA
  • Aspartyl adenylate
  • Aspartyl adenylic acid
  • D-Ribofuranosyl)-9H-purin-6-yl]
  • D-Ribofuranosyl-9H-purin-6-yl) mono(dihydrogen phosphate) (ester)
  • D-Ribofuranosyl-9H-purin-6-yl) mono(dihydrogen phosphoric acid) (ester)
  • N(6)-(1,2-Dicarboxyethyl)-AMP
  • Succinyl AMP
  • Succinyladenosine 5'-monophosphate
  • Succinyladenosine 5'-monophosphoric acid
  • Succinyladenosine monophosphate
  • Succinyladenosine monophosphorate
  • Succinyladenosine monophosphoric acid
Chemical Formula: C14H18N5O11P
Average Molecular Weight: 463.2934
Monoisotopic Molecular Weight: 463.074042955
InChI Key: OFBHPPMPBOJXRT-DPXQIYNJSA-N
InChI:InChI=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
CAS number: 19046-78-7
IUPAC Name:(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
Traditional IUPAC Name: adenylosuccinic acid
SMILES:O[C@@H]1[C@@H](COP(O)(O)=O)O[C@H]([C@@H]1O)N1C=NC2=C1N=CN=C2NC(CC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • 6-alkylaminopurine
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Amino fatty acid
  • Fatty acyl
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.38 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity96.18 m3·mol-1ChemAxon
Polarizability39.42 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenylsuccinic acid <> Adenosine monophosphate + Fumaric acid
L-Aspartic acid + Guanosine triphosphate + Inosinic acid <> Adenylsuccinic acid + Guanosine diphosphate +2 Hydrogen ion + Phosphate
Guanosine triphosphate + Inosinic acid + L-Aspartic acid <> Guanosine diphosphate + Phosphate + Adenylsuccinic acid
Adenylsuccinic acid + SAICAR <> Fumaric acid + Adenosine monophosphate + AICAR
Inosinic acid + L-Aspartic acid + Guanosine triphosphate + L-Aspartic acid > Guanosine diphosphate + Phosphate +2 Hydrogen ion + N(6)-(1,2-dicarboxyethyl)AMP + Adenylsuccinic acid
N(6)-(1,2-dicarboxyethyl)AMP + Adenylsuccinic acid > Fumaric acid + Adenosine monophosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-0091600000-d3ff612cea73450d5c19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0290000000-e7e3d8c35b40ea40e3b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1390000000-f734f11568b018669694View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imj-5080900000-59f4f4d8892f9c1e81f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9180100000-ae2ec357f2c79556d583View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-e788111b4885f014689fView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID15919
HMDB IDHMDB00536
Pubchem Compound ID440122
Kegg IDC03794
ChemSpider ID389122
WikipediaAdenylsuccinate
BioCyc IDNot Available
Ligand Expo2SA