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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-09-03 21:35:42 UTC
HMDB IDHMDB00912
Secondary Accession NumbersNone
Metabolite Identification
Common NameSuccinyladenosine
DescriptionSuccinyladenosine (SAdo) is one of the dephosphorylated enzyme substrate that accumulates in body fluids of patients with adenylosuccinate lyase (ADSL) deficiency, the other being 5-amino-4-imidazole-N-succinocarboxamide riboside (SAICAr). ADSL is an inherited metabolic disease characterized by various degrees of psychomotor retardation. (PMID 15902552 ). The severity of the clinical presentation correlates with a low S-Ado/SAICAr ratio in body fluids. (PMID: 15571235 ). Normally Succinyladenosine is not found in blood or CSF but may be detected in trace amounts in urine. (OMIM 103050 ).
Structure
Thumb
Synonyms
  1. (S)-N-(1,2-dicarboxyethyl)-Adenosine
  2. 6-(1,2-Dicarboxyethylamino)-9-b-D-ribofuranosylpurine
  3. 6-(1,2-Dicarboxyethylamino)-9-beta-delta-ribofuranosylpurine
  4. N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-Aspartate
  5. N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-Aspartic acid
  6. N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-Aspartate
  7. N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-Aspartic acid
  8. N-9-Ribofuranosyl-9H-purin-6-yl-Aspartate
  9. N-9-Ribofuranosyl-9H-purin-6-yl-Aspartic acid
  10. Succinoadenosine
Chemical FormulaC14H17N5O8
Average Molecular Weight383.3135
Monoisotopic Molecular Weight383.107712545
IUPAC Name(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
Traditional Name(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl}amino)butanedioic acid
CAS Registry Number4542-23-8
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N[C@@H](CC(O)=O)C(O)=O)N=CN=C12
InChI Identifier
InChI=1S/C14H17N5O8/c20-2-6-9(23)10(24)13(27-6)19-4-17-8-11(15-3-16-12(8)19)18-5(14(25)26)1-7(21)22/h3-6,9-10,13,20,23-24H,1-2H2,(H,21,22)(H,25,26)(H,15,16,18)/t5-,6+,9+,10+,13+/m0/s1
InChI KeyVKGZCEJTCKHMRL-VWJPMABRSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassGlycoamino Acids and Derivatives
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Purine Nucleosides and Analogues
Substituents
  • 1,2 Diol
  • 1,3 Aminoalcohol
  • Alpha Amino Acid Or Derivative
  • Aminopyrimidine
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • N Glycosyl Compound
  • N Substituted Alpha Amino Acid
  • Oxolane
  • Pentose Monosaccharide
  • Primary Alcohol
  • Purine
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Succinic Acid
Direct ParentGlycoamino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point233 - 238 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.62 g/LALOGPS
logP-1.3ALOGPS
logP-3.9ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.14ChemAxon
pKa (Strongest Basic)4.58ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area200.15ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity85.3ChemAxon
Polarizability34.83ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.1 +/- 5.2 uMInfant (0-1 year old)BothSevere psychomotor delay and autism details
Cerebrospinal Fluid (CSF)Detected and Quantified477.0 uMAdult (>18 years old)Not SpecifiedAdenylosuccinate lyase (ASDL) deficiency details
UrineDetected and Quantified101-188 umol/mmol creatinineAdult (>18 years old)BothAdenylosuccinate lyase (ASDL) deficiency details
Associated Disorders and Diseases
Disease References
Adenylosuccinate lyase deficiency
  1. Marinaki AM, Champion M, Kurian MA, Simmonds HA, Marie S, Vincent MF, van den Berghe G, Duley JA, Fairbanks LD: Adenylosuccinate lyase deficiency--first British case. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1231-3. Pubmed: 15571235
  2. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. Pubmed: 10102915
Autism
  1. Jaeken J, Van den Berghe G: An infantile autistic syndrome characterised by the presence of succinylpurines in body fluids. Lancet. 1984 Nov 10;2(8411):1058-61. Pubmed: 6150139
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022314
KNApSAcK IDNot Available
Chemspider ID17216022
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00912
Metagene LinkHMDB00912
METLIN ID5867
PubChem Compound20849086
PDB IDNot Available
ChEBI ID71169
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. Marinaki AM, Champion M, Kurian MA, Simmonds HA, Marie S, Vincent MF, van den Berghe G, Duley JA, Fairbanks LD: Adenylosuccinate lyase deficiency--first British case. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1231-3. Pubmed: 15571235
  2. Tsuchiya H, Hayashi T, Tatsumi M, Hoshino Y, Ohtani S, Takagi N: High-performance liquid-chromatographic analysis for serotonin and tryptamine excreted in urine after oral loading with L-tryptophan. Clin Chem. 1989 Jan;35(1):43-7. Pubmed: 2910580
  3. Zikanova M, Krijt J, Hartmannova H, Kmoch S: Preparation of 5-amino-4-imidazole-N-succinocarboxamide ribotide, 5-amino-4-imidazole-N-succinocarboxamide riboside and succinyladenosine, compounds usable in diagnosis and research of adenylosuccinate lyase deficiency. J Inherit Metab Dis. 2005;28(4):493-9. Pubmed: 15902552