Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110100
Identification
Name: 5'-phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
Description:An organophosphate oxoanion that is the tetraanionic form of SAICAR. It is the major species at pH 7.3.
Structure
Thumb
Synonyms:
  • (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
  • 1-(5-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
  • 5'-P-ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
  • 5'-p-Ribosyl-4-(N-succinocarboxamide)-5-amino imidazole
  • 1-(5'-phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
  • SAICAR
Chemical Formula: C13H15N4O12P
Average Molecular Weight: 450.26
Monoisotopic Molecular Weight: 454.0737086059
InChI Key: NAQGHJTUZRHGAC-LBGUGVGYSA-J
InChI: InChI=1S/C13H19N4O12P/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27)/p-4/t4?,5-,8-,9-,12-/m1/s1
CAS number: 3031-95-6
IUPAC Name:(2S)-2-[5-amino-1-(5-O-phosphonato-β-D-ribosyl)imidazole-4-carboxamido]succinate
Traditional IUPAC Name: saicar
SMILES:C(OP([O-])([O-])=O)C2(C(O)C(O)C(N1(C(N)=C(C(=O)NC(C([O-])=O)CC([O-])=O)N=C1))O2)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassImidazole ribonucleosides and ribonucleotides
Direct Parent 1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Aspartic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Alpha-amino acid or derivatives
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Imidazolyl carboxylic acid derivative
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Primary aromatic amine
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • N-substituted imidazole
  • Aminoimidazole
  • Monosaccharide
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Vinylogous amide
  • Oxolane
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
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 Solubility1.73 mg/mLALOGPS
logP-1.8ALOGPS
logP-4.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.54ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area263.99 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.65 m3·mol-1ChemAxon
Polarizability38.5 Å3ChemAxon
Number of Rings2ChemAxon
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
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
References
References:
  • Keller KE, Tan IS, Lee YS (2012)SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions. Science (New York, N.Y.) 338, Pubmed: 23086999
  • Keller KE, Doctor ZM, Dwyer ZW, Lee YS (2014)SAICAR induces protein kinase activity of PKM2 that is necessary for sustained proliferative signaling of cancer cells. Molecular cell 53, Pubmed: 24606918
Synthesis Reference: Shaw, Gordon; Thomas, Peter S.; Patey, Carole A. H.; Thomas, Susan E. Purines, pyrimidines and imidazoles. Part 50. Inhibition of adenylosuccinate AMP-lyase no. 4.3.2.2. by derivatives of N-(5-amino-1-b-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate (SAICAR) and virazole 5'-phosphate. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1979), (6), 1415-24.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI58443
HMDBHMDB00797
IAF126044624
KEGGC04823
MetaboLightsMTBLC58443
PubChem45266647