SAICAR (PAMDB000186)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000186
Identification
Name: SAICAR
Description:SAICAR (or (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate) is a substrate for the multifunctional protein ADE2. SAICAR is an intermediate in purine metabolism. (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate is converted from 5-Amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate via phosphoribosylaminoimidazole-succinocarboxamide synthase [EC: 6.3.2.6] or SAICAR synthase. This enzyme catalyses the seventh step out of ten in the biosynthesis of purine nucleotides. (Wikipedia)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
  • (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate
  • (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acid
  • (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinate
  • (S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acid
  • (S)-2-(5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido)succinate
  • (S)-2-(5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido)succinic acid
  • (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate
  • (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid
  • (S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate
  • (S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinic acid
  • (S)-2-[5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido]succinate
  • (S)-2-[5-amino-1-(5-phospho-δ-Ribosyl)imidazole-4-carboxamido]succinic acid
  • 1-(5'-Phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
  • 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
  • 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole
  • 1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole
  • 1-(5-Phosphoribosyl)-4-(N-succino-carboxamide)-5-aminoimidazole
  • 5'-p-Ribosyl-4-(N-succinocarboxamide)-5-amino imidazole
  • 5'-P-Ribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
  • 5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
  • 5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole
  • 5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide
  • L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  • L-N-[(5-amino-1-b-D-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
  • L-N-[(5-amino-1-b-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  • L-N-[(5-amino-1-b-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
  • L-N-[(5-amino-1-b-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  • L-N-[(5-amino-1-b-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
  • L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  • L-N-[(5-amino-1-beta-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
  • L-N-[(5-amino-1-β-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  • L-N-[(5-amino-1-β-δ-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphoric acid)
  • N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartate 5'-phosphate
  • N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate
  • N-(5-amino-1-Ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphoric acid
  • N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartate
  • N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acid
  • Phosphoribosylaminoimidazolesuccinocarboxamide
  • SAICAR
  • SAICAriboside
  • Succino-AICAR
  • Succinylaminoimidazole carboxamide riboside
Chemical Formula: C13H19N4O12P
Average Molecular Weight: 454.2833
Monoisotopic Molecular Weight: 454.073708604
InChI Key: NAQGHJTUZRHGAC-ZZZDFHIKSA-N
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)/t4-,5+,8+,9+,12+/m0/s1
CAS number: 3031-95-6
IUPAC Name:(2S)-2-[({5-amino-1-[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]-1H-imidazol-4-yl}(hydroxy)methylidene)amino]butanedioic acid
Traditional IUPAC Name: (2S)-2-[({5-amino-1-[(3R,4S,5S)-3,4-dihydroxy-5-[hydroxy(phosphono)methyl]oxolan-2-yl]imidazol-4-yl}(hydroxy)methylidene)amino]butanedioic acid
SMILES:NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(=O)N[C@@H](CC(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as imidazole ribonucleosides and ribonucleotides. These are organic compounds in which the C-1 of a?ribosyl?moiety is N-linked to an imidazole ring. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety. This class does not contain benzimidazole nucleosides and nucleotides.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Imidazole ribonucleosides and ribonucleotides
Sub ClassNot Available
Direct Parent Imidazole ribonucleosides and ribonucleotides
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Imidazole ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Primary aromatic amine
  • N-substituted imidazole
  • Dicarboxylic acid or derivatives
  • Saccharide
  • Aminoimidazole
  • Heteroaromatic compound
  • Oxolane
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.72 mg/mLALOGPS
logP-1.8ALOGPS
logP-5.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.25ChemAxon
pKa (Strongest Basic)7.08ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area278.48 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity90.71 m3·mol-1ChemAxon
Polarizability38.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
SAICAR <> Phosphoribosyl formamidocarboxamide + Fumaric acid
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate
SAICAR <> Fumaric acid + AICAR
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid <> ADP + Phosphate + SAICAR
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > ADP + Inorganic phosphate + SAICAR
Adenylsuccinic acid + SAICAR <> Fumaric acid + Adenosine monophosphate + AICAR
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > SAICAR + Phosphate + Adenosine diphosphate + Hydrogen ion + SAICAR + ADP
SAICAR + SAICAR > AICAR + Fumaric acid
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004u-0490700000-86a0d53f872d386acc0bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-6960000000-f6a547b69124d08116b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-4940000000-fd3462a73fc305a5d0f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f7c-2293800000-83e319c3c83a959d977aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000x-3390100000-d322d060609e295ccfa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9420000000-980569ce0c7a7ec24733View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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 a
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18319
HMDB IDHMDB00797
Pubchem Compound ID160666
Kegg IDC04823
ChemSpider ID141175
Wikipedia IDNot Available
BioCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE
EcoCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE