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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 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 KeyInChIKey=OFBHPPMPBOJXRT-DPXQIYNJSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine 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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but 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 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
Polarizability39.51 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
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)Download (PDF)
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. [8412002 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
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 committed step in the biosynthesis of AMP from IMP.
Gene Name:
ADSS
Uniprot ID:
P30520
Molecular weight:
50097.075
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
General function:
Involved in adenylosuccinate synthase activity
Specific function:
Component of the purine nucleotide cycle (PNC), which interconverts IMP and AMP to regulate the nucleotide levels in various tissues, and which contributes to glycolysis and ammoniagenesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP (By similarity).
Gene Name:
ADSSL1
Uniprot ID:
Q8N142
Molecular weight:
50208.16
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails