Phosphoribosylaminoimidazolesuccinocarboxamide

Phosphoribosylaminoimidazolesuccinocarboxamide
Names

Systematic IUPAC name PP(2S)-(5-Amino-1-{(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazole-4-carboxamido)butanedioic acid
Other names SAICAR; 2-[(5-Amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazol-4-yl)formamido]butanedioic acid; N-{[5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-yl]carbonyl}-L-aspartic acid
Identifiers
CAS Number	3031-95-6^Y
3D model (JSmol)	Interactive image
3DMet	B05149
ChEBI	CHEBI:18319^N
ChemSpider	141175^Y
KEGG	C04823^N
MeSH	SAICAR
PubChem CID	160666
UNII	K1PVR64RIF^Y
CompTox Dashboard (EPA)	DTXSID90184404
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^N Key: NAQGHJTUZRHGAC-ZZZDFHIKSA-N^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/s1 Key: NAQGHJTUZRHGAC-ZZZDFHIKBX
SMILES O=C(O)C[C@@H](C(=O)O)NC(=O)c1ncn(c1N)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)COP(=O)(O)O
Properties
Chemical formula	C₁₃H₁₉N₄O₁₂P
Molar mass	454.285 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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.^[1]

References

^ 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:	Ribose 5-phosphate (R5P) Phosphoribosyl pyrophosphate (PRPP) Phosphoribosylamine (PRA) Glycineamide ribonucleotide (GAR) Phosphoribosyl-N-formylglycineamide (FGAR) 5′-Phosphoribosylformylglycinamidine (FGAM) 5-Aminoimidazole ribotide (AIR) 5′-Phosphoribosyl-4-carboxy-5-aminoimidazole (CAIR) Phosphoribosylaminoimidazolesuccinocarboxamide (SAICAR) AICA ribonucleotide (AICAR) 5-Formamidoimidazole-4-carboxamide ribotide (FAICAR)
IMP→AMP:	Adenylosuccinate
IMP→GMP:	Xanthosine monophosphate

catabolism

pyrimidine
metabolism

anabolism

catabolism

uracil:	β-Alanine Dihydrouracil 3-Ureidopropionic acid
thymine:	3-Aminoisobutyric acid Dihydrothymine β-Ureidoisobutyric acid

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