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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-10-23 18:37:13 UTC
HMDB IDHMDB0000912
Secondary Accession Numbers
  • HMDB00912
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
ValueSource
(S)-N-(1,2-Dicarboxyethyl)-adenosineChEBI
6-(1,2-dicarboxyethylamino)-9-beta-D-RibofuranosylpurineChEBI
N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acidChEBI
N-9-Ribofuranosyl-9H-purin-6-yl-aspartic acidChEBI
SuccinoadenosineChEBI
6-(1,2-dicarboxyethylamino)-9-b-D-RibofuranosylpurineGenerator
6-(1,2-dicarboxyethylamino)-9-β-D-ribofuranosylpurineGenerator
N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartateGenerator
N-(9-b-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acidGenerator
N-(9-beta-D-Ribofuranosyl-9H-purin-6-yl)-L-aspartateGenerator
N-(9-β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartateGenerator
N-(9-β-D-ribofuranosyl-9H-purin-6-yl)-L-aspartic acidGenerator
N-9-Ribofuranosyl-9H-purin-6-yl-aspartateGenerator
6-(1,2-dicarboxyethylamino)-9-beta-delta-RibofuranosylpurineHMDB
N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartateHMDB
N-(9-beta-delta-Ribofuranosyl-9H-purin-6-yl)-L-aspartic acidHMDB
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 Nameatp - adenosine triphosphate
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
DescriptionThis compound belongs to the class of chemical entities known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleosides
Direct ParentPurine nucleosides
Alternative Parents
Substituents
  • Purine nucleoside
  • Aspartic acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-alkylaminopurine
  • 6-aminopurine
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • N-substituted imidazole
  • Pyrimidine
  • Imidolactam
  • Oxolane
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Primary alcohol
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Indirect biological role:

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 Area200.15 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity85.3 m³·mol⁻¹ChemAxon
Polarizability34.83 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0l6r-8129000000-a61f85c8b0714ae949d3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ac0-9610066000-c7055bad2597f21774eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0096000000-9b81fa7e1337be93a9f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-0291000000-44075e8e93da0ec9d2f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-1490000000-a88e52cec6ba27380289View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f89-0179000000-ce2528c4b8d13111f498View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0191000000-17fff23d0573f012bc9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zgi-1290000000-dc5ba463b978c4180aabView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0-21 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
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
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 ]