CHEBI:18319 - SAICAR

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ChEBI Name SAICAR
ChEBI ID CHEBI:18319
Definition A 1-(phosphoribosyl)imidazolecarboxamide resulting from the formal condesation of the darboxy group of 5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid with the amino group of L-aspartic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Margaret Duesbury
Secondary ChEBI IDs CHEBI:11028, CHEBI:572, CHEBI:18965, CHEBI:78110
Supplier Information ChemicalBook:CB0406220, ChemicalBook:CB1323708, eMolecules:533977, eMolecules:27677487, eMolecules:474936, Selleckchem:adenine, ZINC000000000882
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Cannabidiol (CBD) is a phytocannabinoid, one of 113 identified cannabinoids in Cannabis, along with tetrahydrocannabinol (THC), and accounts for up to 40% of the plant's extract. Medically, it is an anticonvulsant used to treat multiple forms of epilepsy. It was discovered in 1940 and, as of 2024 clinical research on CBD included studies related to the treatment of anxiety, addiction, psychosis, movement disorders, and pain, but there is insufficient high-quality evidence that CBD is effective for these conditions. CBD is sold as an herbal dietary supplement and promoted with yet unproven claims of particular therapeutic effects. Cannabidiol can be taken internally in multiple ways, including by inhaling cannabis smoke or vapor, swallowing it by mouth, and through use of an aerosol spray into the cheek. It may be supplied as CBD oil containing only CBD as the active ingredient (excluding THC or terpenes), CBD-dominant hemp extract oil, capsules, dried cannabis, or prescription liquid solution. CBD does not have the same psychoactivity as THC, and can modulate the psychoactive effects of THC on the body if both are present. Conversion of CBD to THC can occur when CBD is heated to temperatures between 250–300 °C, potentially leading to its partial transformation into THC. In the United States, the cannabidiol drug Epidiolex was approved by the Food and Drug Administration (FDA) in 2018 for the treatment of two seizure disorders. While the 2018 United States Farm Bill removed hemp and hemp extracts (including CBD) from the Controlled Substances Act, the marketing and sale of CBD formulations for medical use or as an ingredient in dietary supplements or manufactured foods remains illegal under FDA regulation, as of 2024.
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Formula C13H19N4O12P
Net Charge 0
Average Mass 454.28330
Monoisotopic Mass 454.07371
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
InChIKey NAQGHJTUZRHGAC-ZZZDFHIKSA-N
SMILES Nc1c(ncn1[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
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:txid562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing SAICAR (CHEBI:18319) has functional parent succinic acid (CHEBI:15741)
SAICAR (CHEBI:18319) has role Escherichia coli metabolite (CHEBI:76971)
SAICAR (CHEBI:18319) has role mouse metabolite (CHEBI:75771)
SAICAR (CHEBI:18319) is a 1-(phosphoribosyl)imidazolecarboxamide (CHEBI:37290)
SAICAR (CHEBI:18319) is conjugate acid of SAICAR(4−) (CHEBI:58443)
Incoming SAICAR(4−) (CHEBI:58443) is conjugate base of SAICAR (CHEBI:18319)
IUPAC Names
(2S)-2-[5-amino-1-(5-O-phosphono-β-D-ribosyl)imidazole-4-carboxamido]succinic acid
N-{[5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-yl]carbonyl}-L-aspartic acid
Synonyms Sources
(S)-2-[5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido]succinate KEGG COMPOUND
1-(5'-Phosphoribosyl)-4-(N-succinocarboxamide)-5-aminoimidazole KEGG COMPOUND
1-(5'-Phosphoribosyl)-5-amino-4-(N-succinocarboxamide)-imidazole KEGG COMPOUND
5'-Phosphoribosyl-4-(N-succinocarboxamide)-5-aminoimidazole KEGG COMPOUND
SAICA riboside ChEBI
SAICAR KEGG COMPOUND
Succino-AICAR HMDB
succinyl-5-aminoimidazole-4-carboxamide-1-ribose-5-phosphate ChEBI
succinylaminoimidazolecarboxamide ribose-5'-phosphate ChEBI
Manual Xrefs Databases
C04823 KEGG COMPOUND
HMDB0000797 HMDB
P-RIBOSYL-4-SUCCCARB-AMINOIMIDAZOLE MetaCyc
Phosphoribosylaminoimidazolesuccinocarboxamide Wikipedia
View more database links
Registry Number Type Source
3031-95-6 CAS Registry Number ChemIDplus
Citations Types Sources
23086999 PubMed citation Europe PMC
24606918 PubMed citation SUBMITTER
Last Modified
09 December 2024