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Record Information
Version	2.0
Creation Date	2012-05-31 13:01:12 -0600
Update Date	2015-09-17 15:41:06 -0600
Secondary Accession Numbers	ECMDB00797
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x98e55ae0> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Amino acids, peptides, and analogues
Direct Parent	Aspartic acid and derivatives
Alternative Parents	N-acyl-alpha amino acids Imidazole ribonucleosides and ribonucleotides Glycosylamines Imidazolyl carboxylic acids and derivatives N-substituted imidazoles Dicarboxylic acids and derivatives Aminoimidazoles Tetrahydrofurans Organic phosphonic acids Heteroaromatic compounds Secondary alcohols Amino acids 1,2-diols Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Carboxylic acids Carboximidic acids Azacyclic compounds Primary amines Organopnictogen compounds Organophosphorus compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
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 Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 4.72 g/L ALOGPS logP -1.8 ALOGPS logP -5.9 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 1.25 ChemAxon pKa (Strongest Basic) 7.08 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 15 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 278.48 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 90.71 m³·mol⁻¹ ChemAxon Polarizability 38.81 ų ChemAxon Number of Rings 2 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 SAICAR > Fumaric acid + AICAR Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid > Hydrogen ion + 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 5 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate SAICAR <> Fumaric acid + AICAR 5 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate <> SAICAR + ADP + Hydrogen ion + Phosphate
SMPDB Pathways:	purine nucleotides de novo biosynthesis PW000910 purine nucleotides de novo biosynthesis 1435709748 PW000960 purine nucleotides de novo biosynthesis 2 PW002033
KEGG Pathways:	Alanine, aspartate and glutamate metabolism ec00250 Metabolic pathways eco01100 Purine metabolism ec00230
EcoCyc Pathways:	inosine-5'-phosphate biosynthesis I PWY-6123
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004u-0490700000-86a0d53f872d386acc0b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-001i-6960000000-f6a547b69124d08116b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-001l-4940000000-fd3462a73fc305a5d0f3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f7c-2293800000-83e319c3c83a959d977a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-000x-3390100000-d322d060609e295ccfa2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-003u-9420000000-980569ce0c7a7ec24733 View 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
Links
External Links:	Resource Link CHEBI ID 18319 HMDB ID HMDB00797 Pubchem Compound ID 160666 Kegg ID C04823 ChemSpider ID 141175 Wikipedia ID Phosphoribosylaminoimidazolesuccinocarboxamide BioCyc ID P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE EcoCyc ID P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE

Enzymes