Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:27:28 UTC
HMDB IDHMDB00536
Secondary Accession Numbers
  • HMDB01332
  • HMDB11633
Metabolite Identification
Common NameAdenylsuccinic acid
DescriptionAdenylsuccinic acid is a substrate of the enzyme adenylosuccinase [EC 4.3.2.2] in purine metabolism pathway. The accumulation of adenylsuccinic acid in body fluids occurs due to a deficiency of adenylosuccinase. (KEGG; PMID 8412002 ).
Structure
Thumb
Synonyms
  1. 6-Succino-5'-adenylate
  2. 6-Succino-5'-adenylic acid
  3. Adenyl-Succinic acid
  4. Adenylosuccinate
  5. Adenylosuccinic acid
  6. Adenylsuccinate
  7. Adenylsuccinic acid
  8. Aspartyl adenylate
  9. D-Ribofuranosyl)-9H-purin-6-yl]
  10. D-Ribofuranosyl-9H-purin-6-yl) mono(dihydrogen phosphate) (ester)
  11. N(6)-(1,2-Dicarboxyethyl)-AMP
  12. Succinyl AMP
  13. Succinyladenosine 5'-monophosphate
  14. Succinyladenosine monophosphorate
  15. Succinyladenosine monophosphoric acid
Chemical FormulaC14H18N5O11P
Average Molecular Weight463.2934
Monoisotopic Molecular Weight463.074042955
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
CAS Registry Number19046-78-7
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
InChI Identifier
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
InChI KeyOFBHPPMPBOJXRT-DPXQIYNJSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • purine ribonucleoside 5'-monophosphate(ChEBI)
Substituents
  • 1,2 Diol
  • 1,3 Aminoalcohol
  • 1 Phosphoribosyl Imidazole
  • Alpha Amino Acid Or Derivative
  • Aminopyrimidine
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Glyco Amino Acid
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • N Substituted Alpha Amino Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Succinic Acid
Direct ParentPurine Ribonucleoside Monophosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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 area246.68ChemAxon
rotatable bond count9ChemAxon
refractivity96.18ChemAxon
polarizability39.51ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Aspartate MetabolismSMP00067map00250
Purine MetabolismSMP00050map00230
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022101
KNApSAcK IDNot Available
Chemspider ID389122
KEGG Compound IDC03794
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAdenylsuccinate
NuGOwiki LinkHMDB00536
Metagene LinkHMDB00536
METLIN ID5521
PubChem Compound440122
PDB IDNot Available
ChEBI ID15919
References
Synthesis ReferenceBuck, 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)Not Available
General References
  1. Van den Bergh F, Vincent MF, Jaeken J, Van den Berghe G: Residual adenylosuccinase activities in fibroblasts of adenylosuccinase-deficient children: parallel deficiency with adenylosuccinate and succinyl-AICAR in profoundly retarded patients and non-parallel deficiency in a mildly retarded girl. J Inherit Metab Dis. 1993;16(2):415-24. Pubmed: 8412002

Enzymes

Gene Name:
ADSL
Uniprot ID:
P30566
Gene Name:
ADSS
Uniprot ID:
P30520
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Gene Name:
ADSSL1
Uniprot ID:
Q8N142
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails