You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-05-06 20:38:30 UTC
HMDB IDHMDB0000536
Secondary Accession Numbers
  • HMDB0001332
  • HMDB0011633
  • HMDB00536
  • HMDB0059653
  • HMDB01332
  • HMDB11633
  • HMDB59653
Metabolite Identification
Common NameAdenylsuccinic acid
DescriptionAdenylsuccinic acid, also known as adenylosuccinate or aspartyl adenylate, 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. Adenylsuccinic acid is a strong basic compound (based on its pKa). Within humans, adenylsuccinic acid participates in a number of enzymatic reactions. In particular, adenylsuccinic acid can be converted into fumaric acid through its interaction with the enzyme adenylosuccinate lyase. In addition, adenylsuccinic acid can be biosynthesized from inosinic acid and L-aspartic acid which is catalyzed by the enzyme adenylosuccinate synthetase. Adenylosuccinate is an intermediate in the interconversion of the purine nucleotides inosine monophosphate (IMP) and adenosine monophosphate (AMP). GTP is used instead of adenosine triphosphate (ATP), so the reaction is not dependent on its products. The enzyme adenylosuccinate synthase carries out the reaction by the addition of aspartate to IMP and requires the input of energy from a phosphoanhydride bond in the form of guanosine triphosphate (GTP). Adenylsuccinic acid is a substrate of the enzyme adenylosuccinase (EC 4.3.2.2) in purine metabolism. The accumulation of adenylsuccinic acid in bodily fluids occurs due to a deficiency of adenylosuccinase (PMID: 8412002 ).
Structure
Data?1588797510
Synonyms
ValueSource
N6-(1,2-Dicarboxyethyl)AMPKegg
AdenylosuccinateKegg
Adenylosuccinic acidKegg
Aspartyl adenylateHMDB
6-Succino-5'-adenylic acidHMDB
6-Succino-5’-adenylic acidHMDB
Adenylsuccinic acidHMDB
N-[9-(5-O-Phosphono-beta-D-ribofuranosyl)-9H-purin-6-yl]-L-aspartic acidHMDB
N-[9-(5-O-Phosphono-beta-D-ribofuranosyl)-9H-purin-6-yl]aspartic acidHMDB
N-[9-(5-O-Phosphono-β-D-ribofuranosyl)-9H-purin-6-yl]-L-aspartic acidHMDB
N-[9-(5-O-Phosphono-β-D-ribofuranosyl)-9H-purin-6-yl]aspartic acidHMDB
Succinyl AMPHMDB
Succinyladenosine 5'-monophosphateHMDB
Succinyladenosine 5’-monophosphateHMDB
Succinyladenosine monophosphoric acidHMDB
Chemical FormulaC14H18N5O11P
Average Molecular Weight463.2934
Monoisotopic Molecular Weight463.074042955
IUPAC Name(2S)-2-({9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-9H-purin-6-yl}amino)butanedioic acid
Traditional Nameadenylosuccinic acid
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=C2N[C@@H](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+/m0/s1
InChI KeyOFBHPPMPBOJXRT-VWJPMABRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBiphenyls and derivatives
Direct ParentBiphenyls and derivatives
Alternative Parents
Substituents
  • Biphenyl
  • Alpha-amino acid or derivatives
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Medium-chain fatty acid
  • Alkyl aryl ether
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Organosulfonic acid amide
  • Aminosulfonyl compound
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

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-4.8ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)3.81ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area246.68 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity96.18 m³·mol⁻¹ChemAxon
Polarizability39.41 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kb-9711800000-86455d261bccbe67da62Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03xs-5101029000-a7bb5fbca95271f9a4bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0000900000-682db2581239b5c0a595Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-03di-0000900000-ab92d302fce66b902faaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-01ot-7143900000-e73b0c364a41781e7287Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9420000000-b8052106219be7dd584eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-005a-9500000000-83812f91a1e7849cdf9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-0090000000-46a1360de4b17c75e2e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9550000000-e31a634109a93503ef6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-9700000000-976efe169398b143430fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0059-9600000000-da7d432450879199d87aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9300000000-432a2295a3e2d9e5e196Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0000900000-3303cf34d7c785b2bd2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0w29-0080900000-ed11d2f1a5b98f01a24bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0090000000-e04eacd49705ed3253bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0290000000-8e84bc7ec6914f71a462Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0ikl-1940000000-d1f576d2848684937eb3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0190000000-4db35b93ee46253bf027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-0091600000-d3ff612cea73450d5c19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-0290000000-e7e3d8c35b40ea40e3b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1390000000-f734f11568b018669694Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0imj-5080900000-59f4f4d8892f9c1e81f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fb9-9180100000-ae2ec357f2c79556d583Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-e788111b4885f014689fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04418
Phenol Explorer Compound IDNot Available
FooDB IDFDB022101
KNApSAcK IDC00007229
Chemspider ID394323
KEGG Compound IDC03794
BioCyc IDADENYLOSUCC
BiGG IDNot Available
Wikipedia LinkAdenylosuccinate
METLIN IDNot Available
PubChem Compound447145
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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. [PubMed:8412002 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
Reactions
Adenylsuccinic acid → Fumaric acid + Adenosine monophosphatedetails
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 + Phosphate + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Phosphate + 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 + Phosphate + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid → Guanosine diphosphate + Phosphate + Adenylsuccinic aciddetails