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Phosphoribosylaminoimidazolesuccinocarboxamide

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Phosphoribosylaminoimidazolesuccinocarboxamide
Names
Systematic IUPAC name PP(2S)-(5-Amino-1-{(2R,3R,4S,5R)-3,4-dihydroxy-5-oxolan-2-yl}-1H-imidazole-4-carboxamido)butanedioic acid
Other names SAICAR; 2-oxolan-2-yl}imidazol-4-yl)formamido]butanedioic acid; N-{carbonyl}-L-aspartic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH SAICAR
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: NAQGHJTUZRHGAC-ZZZDFHIKSA-N
  • InChI=1/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/s1Key: NAQGHJTUZRHGAC-ZZZDFHIKBX
SMILES
  • O=C(O)C(C(=O)O)NC(=O)c1ncn(c1N)2O((O)2O)COP(=O)(O)O
Properties
Chemical formula C13H19N4O12P
Molar mass 454.285 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Phosphoribosylaminoimidazolesuccinocarboxamide (SAICAR) is an intermediate in the formation of purines. The conversion of ATP, L-aspartate, and 5-aminoimidazole-4-carboxyribonucleotide (CAIR) to 5-aminoimidazole-4-(N-succinylcarboxamide) ribonucleotide, ADP, and phosphate by phosphoribosylaminoimidazolesuccinocarboxamide synthetase (SAICAR synthetase) represents the eighth step of de novo purine nucleotide biosynthesis.

References

  1. Scott W. Nelson; Daniel J. Binkowski; Richard B. Honzatko; Herbert J. Fromm (2005). "Mechanism of Action of Escherichia coli Phosphoribosylaminoimidazolesuccinocarboxamide Synthetase". Biochemistry. 44 (2): 766–774. doi:10.1021/bi048191w. PMID 15641804. S2CID 41673787.
Nucleotide metabolic intermediates
purine
metabolism
anabolism
R5P→IMP:
IMP→AMP:Adenylosuccinate
IMP→GMP:Xanthosine monophosphate
catabolism
pyrimidine
metabolism
anabolism
catabolism
uracil:
thymine:


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