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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.

In the quiz scene of the popular Vocaloid song Mesmerizer, the chemical’s name is spelled out. The beginning letter combined with that of the other three words before it spells out “HELP”. In addition, the fourth letter combined with that of the second and third words spell out “SOS”. Furthermore, the use of the chemical’s name might be a sign of Teto telling the viewer that Miku is no longer human.

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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