adenylo-succinate (PAMDB110480)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110480
Identification
Name: adenylo-succinate
Description:The N6-(1,2-dicarboxyethyl) derivative of adenosine 5'-monophosphate.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • N6-(1,2-dicarboxyethyl)-AMP
  • adenylo-succ
Chemical Formula: C14H14N5O11P
Average Molecular Weight: 459.26
Monoisotopic Molecular Weight: 463.0740429569
InChI Key: OFBHPPMPBOJXRT-DPXQIYNJSA-J
InChI: 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)/p-4/t5?,6-,9-,10-,13-/m1/s1
CAS number: 19046-78-7
IUPAC Name:N-[9-(5-O-phosphono-β-D-ribofuranosyl)-9H-purin-6-yl]aspartic acid
Traditional IUPAC Name: adenylosuccinate
SMILES:C(OP(=O)([O-])[O-])C1(OC(C(O)C(O)1)N3(C=NC2(C(=NC=NC=23)NC(CC(=O)[O-])C(=O)[O-])))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine ribonucleoside monophosphates
Alternative Parents
Substituents
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Aspartic acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-alkylaminopurine
  • Monosaccharide phosphate
  • Alpha-amino acid or derivatives
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Secondary aliphatic/aromatic amine
  • Pyrimidine
  • N-substituted imidazole
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Imidolactam
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Oxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.38 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity96.18 m3·mol-1ChemAxon
Polarizability39.51 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0ik9-0040900000-b82cfa15a82a71e3a806View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0190000000-9bcb8baa6f6c26df4465View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03du-0920000000-f57e5dc2c827d4094209View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Nomura Y, Nozawa A, Tozawa Y (2014)Biochemical analyses of ppGpp effect on adenylosuccinate synthetases, key enzymes in purine biosynthesis in rice. Bioscience, biotechnology, and biochemistry 78, Pubmed: 25036129
  • Boitz JM, Strasser R, Yates PA, Jardim A, Ullman B (2013)Adenylosuccinate synthetase and adenylosuccinate lyase deficiencies trigger growth and infectivity deficits in Leishmania donovani. The Journal of biological chemistry 288, Pubmed: 23404497
Synthesis Reference: Buck, 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)
External Links:
ResourceLink
CAS19240-42-7
ChEBI7405
HMDBHMDB00536
IAF126042544
KEGGC03794
MetaboLightsMTBLC57567
PubChem25245432