Record Information
Version2.0
Creation Date2012-05-31 13:01:12 -0600
Update Date2015-09-17 15:41:06 -0600
Secondary Accession Numbers
  • ECMDB00797
Identification
Name:SAICAR
DescriptionSAICAR (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
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
Weight:Average: 454.2833
Monoisotopic: 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
Description belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAspartic acid and derivatives
Alternative Parents
Substituents
  • Aspartic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Imidazole ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Imidazolyl carboxylic acid derivative
  • N-substituted imidazole
  • Dicarboxylic acid or derivatives
  • Aminoimidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Organophosphonic acid derivative
  • Organophosphonic acid
  • Imidazole
  • Azole
  • Amino acid
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.72 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity90.71 m³·mol⁻¹ChemAxon
Polarizability38.81 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
purine nucleotides de novo biosynthesisPW000910 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 1435709748PW000960 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesis 2PW002033 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • inosine-5'-phosphate biosynthesis I PWY-6123
Concentrations
Not Available
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 IDPhosphoribosylaminoimidazolesuccinocarboxamide
BioCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE
EcoCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE

Enzymes

General function:
Involved in ATP binding
Specific function:
ATP + 5-amino-1-(5-phospho-D- ribosyl)imidazole-4-carboxylate + L-aspartate = ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxamido)succinate
Gene Name:
purC
Uniprot ID:
P0A7D7
Molecular weight:
26995
Reactions
ATP + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-aspartate = ADP + phosphate + (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate.
General function:
Involved in N6-(1,2-dicarboxyethyl)AMP AMP-lyase (fumarate-forming) activity
Specific function:
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:
purB
Uniprot ID:
P0AB89
Molecular weight:
51542
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.