Record Information
Version1.0
Created at2020-04-17 18:44:45 UTC
Updated at2020-12-07 19:11:08 UTC
CannabisDB IDCDB004865
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common 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. SAICAR is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
Synonyms
ValueSource
(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
Chemical FormulaC13H19N4O12P
Average Molecular Weight454.28
Monoisotopic Molecular Weight454.0737
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 Namesaicar
CAS Registry Number3031-95-6
SMILES
NC1=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
InChI Identifier
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
InChI KeyNAQGHJTUZRHGAC-ZZZDFHIKSA-N
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSAICAR, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05n1-9732500000-f3a7f13b1dee5f81c7a8Spectrum
Predicted GC-MSSAICAR, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05ot-9600116000-74a62efcb34072bbe352Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-055o-1592600000-05db249dfb0f14143f9fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-3950000000-6ebf6a64483dd1392782Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001l-5940000000-e218e278f5195eb90341Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ug3-6381900000-4fec69ff813fe652ea7dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9350000000-e4e387627fbca1ef1201Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-95f6153e96335a5d2b32Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Adenylosuccinate lyaseADSL22q13.2P30566 details
Multifunctional protein ADE2PAICS4q12P22234 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000797
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022251
KNApSAcK IDNot Available
Chemspider ID141175
KEGG Compound IDC04823
BioCyc IDP-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE
BiGG ID44624
Wikipedia LinkPhosphoribosylaminoimidazolesuccinocarboxamide
METLIN ID5762
PubChem Compound160666
PDB IDNot Available
ChEBI ID18319
References
General References
  1. Keller KE, Tan IS, Lee YS: SAICAR stimulates pyruvate kinase isoform M2 and promotes cancer cell survival in glucose-limited conditions. Science. 2012 Nov 23;338(6110):1069-72. doi: 10.1126/science.1224409. Epub 2012 Oct 18. [PubMed:23086999 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
Not Available
Gene Name:
PAICS
Uniprot ID:
P22234
Molecular weight:
47078.82