Human Metabolome Database Version 3.5

Showing metabocard for Adenylsuccinic acid (HMDB00536)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:27:28 -0600
HMDB ID HMDB00536
Secondary Accession Numbers
  • HMDB01332
  • HMDB11633
Metabolite Identification
Common Name Adenylsuccinic acid
Description Adenylsuccinic 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 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C14H18N5O11P
Average Molecular Weight 463.2934
Monoisotopic Molecular Weight 463.074042955
IUPAC Name 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 adenylosuccinate
CAS Registry Number 19046-78-7
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 Key OFBHPPMPBOJXRT-DPXQIYNJSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Purine Nucleotides
Sub Class Purine 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 Parent Purine Ribonucleoside Monophosphates
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.38 g/L ALOGPS
LogP -1.96 ALOGPS
LogP -5.3 ChemAxon
LogS -2.29 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) 4.58 ChemAxon
Hydrogen Acceptor Count 14 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 246.68 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 96.18 ChemAxon
Polarizability 39.51 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Aspartate Metabolism SMP00067 map00250 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022101
KNApSAcK ID Not Available
Chemspider ID 389122 Link_out
KEGG Compound ID C03794 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Adenylsuccinate Link_out
NuGOwiki Link HMDB00536 Link_out
Metagene Link HMDB00536 Link_out
METLIN ID 5521 Link_out
PubChem Compound 440122 Link_out
PDB ID Not Available
ChEBI ID 15919 Link_out
References
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)
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 Link_out

Enzymes
Name: Adenylosuccinate lyase
Reactions: Not Available
Gene Name: ADSL
Uniprot ID: P30566 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylosuccinate synthetase isozyme 2
Reactions:
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic acid details
Gene Name: ADSS
Uniprot ID: P30520 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylosuccinate synthetase isozyme 1
Reactions:
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic acid details
Gene Name: ADSSL1
Uniprot ID: Q8N142 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA