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SAICAR (YMDB00350)

Identification
YMDB IDYMDB00350
NameSAICAR
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionSAICAR, also known as saicaribotide or succino-aicar, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. SAICAR is a strong basic compound (based on its pKa). SAICAR exists in all eukaryotes, ranging from yeast to humans. SAICAR is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
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)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-D-ribosyl)imidazole-4-carboxamido]succinate
  • (S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinate
  • 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
  • 5-Amino-4-imidazole-N-succinocarboxamide ribonucleotide
  • 5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole
  • 5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazole
  • L-N-[(5-amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  • L-N-[(5-amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)
  • N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphate
  • 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
  • (2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acid
  • Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate
  • Succinylaminoimidazolecarboxamide ribose-5'-phosphate
  • (2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinate
  • (2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acid
  • (2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinate
  • (2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinate
  • (2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acid
  • (S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acid
  • Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acid
  • Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acid
  • Succinyl-aicar
  • N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphate
  • 5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazole
  • SAICAR, (D)-isomer
  • SAICAribotide
  • Succinylaminoimidazole carboxamide ribotide
  • SAICA ribotide
CAS number3031-95-6
WeightAverage: 454.2833
Monoisotopic: 454.073708604
InChI KeyNAQGHJTUZRHGAC-ZZZDFHIKSA-N
InChIInChI=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
IUPAC Name(2S)-2-({5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioic acid
Traditional IUPAC Namesaicar
Chemical FormulaC13H19N4O12P
SMILES[H]OC(=O)C([H])([H])[C@]([H])(N([H])C(=O)C1=C(N([H])[H])N(C([H])=N1)[C@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@@]1([H])O[H])C(=O)O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose-5-phosphate
  • Pentose phosphate
  • Aspartic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Alpha-amino acid or derivatives
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Imidazolyl carboxylic acid derivative
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Aminoimidazole
  • Monosaccharide
  • Imidazole
  • Heteroaromatic compound
  • Azole
  • Vinylogous amide
  • Tetrahydrofuran
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • 1,2-diol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.73 g/LALOGPS
logP-1.8ALOGPS
logP-4.8ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.54ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area263.99 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.65 m³·mol⁻¹ChemAxon
Polarizability38.5 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB Reactions
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate → SAICAR + phosphate + ADP + hydron
SAICAR → 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + Fumaric acid
KEGG Reactions
SAICAR ↔ 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + Fumaric acid
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid + Adenosine triphosphate ↔ SAICAR + phosphate + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
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
External Links:
ResourceLink
CHEBI ID18319
HMDB IDHMDB00797
Pubchem Compound ID160666
Kegg IDC04823
ChemSpider ID24785272
FOODB IDFDB022251
WikipediaSAICAR
BioCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE

Enzymes

Protein Details
1. Adenylosuccinate lyase
General function:
Involved in catalytic activity
Specific function:
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:
ADE13
Uniprot ID:
Q05911
Molecular weight:
54509.89844
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.
Protein Details
2. Phosphoribosylaminoimidazole-succinocarboxamide synthase
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:
ADE1
Uniprot ID:
P27616
Molecular weight:
34603.10156
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.