Record Information
Version1.0
Creation date2011-09-21 00:10:54 UTC
Update date2020-09-17 15:38:42 UTC
Primary IDFDB022251
Secondary Accession Numbers
  • FDB030551
Chemical Information
FooDB NameSAICAR
DescriptionSAICAR, also known as succino-aicar or saicaribotide, 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. Many affected children with organic acidemias experience intellectual disability or delayed development. SAICAR is a strong basic compound (based on its pKa). SAICAR exists in all eukaryotes, ranging from yeast to humans. Within humans, SAICAR participates in a number of enzymatic reactions. In particular, SAICAR can be biosynthesized from 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate and L-aspartic acid through its interaction with the enzyme multifunctional protein ADE2. In addition, SAICAR can be converted into fumaric acid and AICAR; which is catalyzed by the enzyme adenylosuccinate lyase. When present in sufficiently high levels, SAICAR can act as an oncometabolite, a metabotoxin, and an acidogen. In humans, SAICAR is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Outside of the human body, SAICAR has been detected, but not quantified in, several different foods, such as canola, sago palms, cashew nuts, giant butterburs, and swedes. This could make SAICAR a potential biomarker for the consumption of these foods. SAICAR (or (S)-2-succinate) is a substrate for the multifunctional protein ADE2. SAICAR is a potentially toxic compound. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. SAICAR, with regard to humans, has been linked to several inborn metabolic disorders including fumarase deficiency and atic deficiency. These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. As an oncometabolite, high levels of SAICAR stimulate pyruvate kinase isoform M2 and promote cancer cell survival in glucose-limited conditions such as aerobic glycolysis (PMID: 23086999). SAICAR is an intermediate in purine metabolism. As an organic acid, SAICAR is associated with acidosis.
CAS Number3031-95-6
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinic acidChEBI
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinateChEBI
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazoleChEBI
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazoleChEBI
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazoleChEBI
Succino-aicarChEBI
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphateChEBI
Succinylaminoimidazolecarboxamide ribose-5'-phosphateChEBI
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamido]succinic acidGenerator
(2S)-2-[5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamido]succinic acidGenerator
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinic acidGenerator
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphoric acidGenerator
Succinylaminoimidazolecarboxamide ribose-5'-phosphoric acidGenerator
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinateHMDB
(S)-2-(5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acidHMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinateHMDB
(S)-2-(5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acidHMDB
(S)-2-[5-Amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido]succinateHMDB
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazoleHMDB
5'-Phosphoribosyl-4-(N-succinocarbozamide)-5-aminoimidazoleHMDB
5-Amino-4-imidazole-N-succinocarboxamide ribonucleotideHMDB
L-N-[(5-Amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)HMDB
L-N-[(5-Amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)HMDB
N-(5-Amino-1-ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-phosphateHMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartateHMDB
N-[5-Amino-1-(5'-phosphoribofuranosyl)-4-imidazolecarbonyl]aspartic acidHMDB
PhosphoribosylaminoimidazolesuccinocarboxamideHMDB
N-(5-Amino-1-beta-D-ribofuranosylimidazole-4-carbonyl)-L-aspartic acid 5'-phosphateHMDB
5'-Phosphoribosyl-4-(N-succinylcarboxamide)-5-aminoimidazoleHMDB
SAICAR, (D)-isomerHMDB
SAICAribotideHMDB
Succinylaminoimidazole carboxamide ribotideHMDB
SAICA ribotideHMDB
Succinylaminoimidazolecarboxamide ribose-5’-phosphateHMDB
(2S)-2-[5-amino-1-(5-O-b-D-Ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-amino-1-(5-O-b-D-Ribosyl)imidazole-4-carboxamido]succinic acidGenerator
(2S)-2-[5-amino-1-(5-O-beta-D-Ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-amino-1-(5-O-beta-D-Ribosyl)imidazole-4-carboxamido]succinic acidChEBI
(2S)-2-[5-amino-1-(5-O-β-D-ribosyl)imidazole-4-carboxamido]succinateGenerator
(2S)-2-[5-amino-1-(5-O-β-D-ribosyl)imidazole-4-carboxamido]succinic acidGenerator
(S)-2-(5-amino-1-(5-O-D-Ribosyl)imidazole-4-carboxamido)succinateHMDB
(S)-2-(5-amino-1-(5-O-D-Ribosyl)imidazole-4-carboxamido)succinic acidHMDB
(S)-2-(5-amino-1-(5-O-delta-Ribosyl)imidazole-4-carboxamido)succinateHMDB
(S)-2-(5-amino-1-(5-O-delta-Ribosyl)imidazole-4-carboxamido)succinic acidHMDB
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinatehmdb
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinic acidhmdb
(S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinatehmdb
(S)-2-(5-amino-1-(5-phospho-delta-ribosyl)imidazole-4-carboxamido)succinic acidhmdb
(S)-2-[5-amino-1-(5-O-D-Ribosyl)imidazole-4-carboxamido]succinateChEBI
(S)-2-[5-amino-1-(5-O-D-Ribosyl)imidazole-4-carboxamido]succinic acidGenerator
(S)-2-[5-amino-1-(5-O-delta-Ribosyl)imidazole-4-carboxamido]succinateHMDB
1-(5'-Oribosyl)-4-(N-succinocarboxamide)-5-aminoimidazoleChEBI
1-(5'-Oribosyl)-5-amino-4-(N-succinocarboxamide)-imidazoleChEBI
1-(5'-Oribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-oribosyl)-4-(N-succinocarboxamide)-5-aminoimidazoleHMDB
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole' 1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazolehmdb
5'-Oribosyl-4-(N-succinocarboxamide)-5-aminoimidazoleChEBI
5'-Oribosyl-4-(N-succinocarbozamide)-5-aminoimidazoleHMDB
L-N-[(5-amino-1-b-D-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen ate)HMDB
L-N-[(5-amino-1-b-D-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)hmdb
L-N-[(5-amino-1-beta-delta-Ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen ate)HMDB
L-N-[(5-amino-1-beta-delta-ribofuranosylimidazol-4-yl)carbonyl]-5'-(dihydrogen phosphate)hmdb
N-(5-amino-1-Ribofuranosylimidazol-4-ylcarbonyl)aspartic acid 5'-ateHMDB
N-[5-amino-1-(5'-Oribofuranosyl)-4-imidazolecarbonyl]aspartateHMDB
N-[5-amino-1-(5'-Oribofuranosyl)-4-imidazolecarbonyl]aspartic acidHMDB
OribosylaminoimidazolesuccinocarboxamideHMDB
SAICARhmdb
SAICAribosidehmdb
Succino-AICARhmdb
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-ateChEBI
Succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-ic acidGenerator
Succinylaminoimidazole carboxamide ribosidehmdb
Succinylaminoimidazolecarboxamide ribose-5'-ateChEBI
Succinylaminoimidazolecarboxamide ribose-5'-ic acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC13H19N4O12P
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
InChI IdentifierInChI=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
InChI KeyNAQGHJTUZRHGAC-ZZZDFHIKSA-N
Isomeric SMILESNC1=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
Average Molecular Weight454.2833
Monoisotopic Molecular Weight454.073708604
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Indirect biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05n1-9732500000-f3a7f13b1dee5f81c7a8JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-05ot-9600116000-74a62efcb34072bbe352JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-055o-1592600000-05db249dfb0f14143f9fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3950000000-6ebf6a64483dd1392782JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-5940000000-e218e278f5195eb90341JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug3-6381900000-4fec69ff813fe652ea7dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9350000000-e4e387627fbca1ef1201JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-95f6153e96335a5d2b32JSpectraViewer
ChemSpider ID141175
ChEMBL IDNot Available
KEGG Compound IDC04823
Pubchem Compound ID160666
Pubchem Substance IDNot Available
ChEBI ID18319
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00797
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID44624
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Adenylosuccinate lyaseADSLP30566
Multifunctional protein ADE2PAICSP22234
Pathways
NameSMPDB LinkKEGG Link
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference