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Identification
YMDB IDYMDB00871
NameN6-(1,2-Dicarboxyethyl)-AMP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionAdenylosuccinate (N6-(1,2-Dicarboxyethyl)-AMP) is an intermediate in the intercoversion 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 and requires the input of energy from a phosphoanhydride bond in the form of guanosine triphosphate (GTP).[1] GTP is used instead of adenosine triphosphate (ATP), so the reaction is not dependent on its products.[Wikipedia]
Structure
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Synonyms
  • 6-Succino-5'-adenylate
  • 6-Succino-5'-adenylic acid
  • adenyl-Succinic acid
  • adenylosuccinate
  • adenylosuccinic acid
  • Adenylsuccinate
  • Adenylsuccinic acid
  • Aspartyl adenylate
  • D-ribofuranosyl)-9H-purin-6-yl]
  • N(6)-(1,2-dicarboxyethyl)-AMP
  • N(6)-(1,2-dicarboxyethyl)AMP
  • N6-(1,2-dicarboxyethyl)-AMP
  • N6-(1,2-Dicarboxyethyl)AMP
  • Succinyl AMP
  • Succinyladenosine 5'-monophosphate
  • Succinyladenosine monophosphorate
  • Succinyladenosine monophosphoric acid
CAS number19046-78-7
WeightAverage: 463.2934
Monoisotopic: 463.074042955
InChI KeyOFBHPPMPBOJXRT-VWJPMABRSA-N
InChIInChI=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
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 IUPAC Nameadenylosuccinic acid
Chemical FormulaC14H18N5O11P
SMILESO[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
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
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.38 g/LALOGPS
logP-2ALOGPS
logP-5.3ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.58ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area246.68 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity96.18 m³·mol⁻¹ChemAxon
Polarizability39.42 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Alanine, aspartate and glutamate metabolismec00250 Map00250
Purine metabolismec00230 Map00230
SMPDB Reactions
Inosinic acid + L-Aspartic acid + GTPGuanosine diphosphate + phosphate + hydron + N6-(1,2-Dicarboxyethyl)-AMP
N6-(1,2-Dicarboxyethyl)-AMPFumaric acid + Adenosine monophosphate
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Porter, D. J., Rudie, N. G., Bright, H. J. (1983). "Nitro analogs of substrates for adenylosuccinate synthetase and adenylosuccinate lyase." Arch Biochem Biophys 225:157-163.6351751
  • CARTER, C. E., COHEN, L. H. (1956). "The preparation and properties of adenylosuccinase and adenylosuccinic acid." J Biol Chem 222:17-30.13366975
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID15919
HMDB IDHMDB00536
Pubchem Compound ID447145
Kegg IDC03794
ChemSpider ID24784987
FOODB IDNot Available
WikipediaAdenylsuccinate
BioCyc IDNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:
ADE13
Uniprot ID:
Q05911
Molecular weight:
54509.89844
Reactions
N(6)-(1,2-dicarboxyethyl)AMP → fumarate + AMP.
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate → fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.