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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-09 22:33:12 UTC
NP-MRD IDNP0000223
Secondary Accession NumbersNone
Natural Product Identification
Common NameAdenylsuccinic acid
DescriptionAdenylsuccinic acid, also known as adenylosuccinate, succinyladenosine 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 found in all living organisms, ranging from bacteria to plants to animals. Adenylsuccinic acid is an important intermediate in the de novo purine biosynthesis pathway. Specifically, adenylsuccinic acid is an intermediate in the interconversion of purine nucleotides inosine monophosphate (IMP) and adenosine monophosphate (AMP). The enzyme adenylosuccinate synthase carries out the reaction by the addition of aspartate to IMP. This reaction requires the input of energy from a phosphoanhydride bond in the form of guanosine triphosphate (GTP). Adenylsuccinic acid is a substrate least one other important metabolic reaction in purine biosynthesis. In particular, adenylsuccinic acid can be converted into fumaric acid through its interaction with the enzyme known as adenylosuccinate lyase (or adenylosuccinase). Adenylosuccinate lyase deficiency, is a rare autosomal recessive metabolic disorder characterized by the appearance of succinylaminoimidazolecarboxamide riboside (SAICA riboside) and adenylsuccinic acid in cerebrospinal fluid and urine (PMID: 8412002 ). Adenylosuccinate lyase deficiency presents with varying degrees of psychomotor retardation, autism, muscle wasting, and epilepsy. The exact cause of the symptoms is unknown, but possibilities include not enough purine nucleotide synthesis for cell replication, malfunctioning of the purine nucleotide cycle, and a buildup of substrates to toxic levels.
Structure
Thumb
Synonyms
ValueSource
N6-(1,2-Dicarboxyethyl)AMPKegg
AdenylosuccinateKegg
Adenylosuccinic acidKegg
AdenylsuccinateGenerator
Aspartyl adenylateHMDB
6-Succino-5'-adenylic acidHMDB
6-Succino-5’-adenylic 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
Adenylsuccinic acidHMDB
Chemical FormulaC14H18N5O11P
Average Mass463.2934 Da
Monoisotopic Mass463.07404 Da
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=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 KeyOFBHPPMPBOJXRT-DPXQIYNJSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Apis ceranaLOTUS Database
Arabidopsis thalianaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Penicillium chrysogenumLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Escherichia coli K12KNApSAcK Database
Chemical Taxonomy
Description 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
  • Pentose-5-phosphate
  • Pentose phosphate
  • Aspartic acid or derivatives
  • N-glycosyl compound
  • 6-alkylaminopurine
  • Glycosyl compound
  • L-alpha-amino acid
  • Monosaccharide phosphate
  • Alpha-amino acid or derivatives
  • Pentose monosaccharide
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary alcohol
  • Amino acid or derivatives
  • Amino acid
  • 1,2-diol
  • Azacycle
  • Oxacycle
  • Secondary amine
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
HMDB IDHMDB0000536
DrugBank IDDB04418
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  2. Chen Z, Gao Y, Huang X, Yao Y, Chen K, Zeng S, Mao W: Tissue-based metabolomics reveals metabolic biomarkers and potential therapeutic targets for esophageal squamous cell carcinoma. J Pharm Biomed Anal. 2021 Apr 15;197:113937. doi: 10.1016/j.jpba.2021.113937. Epub 2021 Feb 5. [PubMed:33609949 ]