CHEBI:16625 - methylmalonyl-CoA

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name methylmalonyl-CoA
ChEBI ID CHEBI:16625
Definition A member of the class of malonyl-CoAs that is malonyl-CoA carrying a methyl group on the malony side chain.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:14604, CHEBI:6882, CHEBI:19683
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 C25H40N7O19P3S
Net Charge 0
Average Mass 867.60700
Monoisotopic Mass 867.13125
InChI InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12?,13-,16-,17-,18+,22-/m1/s1
InChIKey MZFOKIKEPGUZEN-FBMOWMAESA-N
SMILES CC(C(O)=O)C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)n1cnc2c(N)ncnc12
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Chemical Role(s): acyl donor
Any donor that can transfer acyl groups between molecular entities.
(via acyl-CoA )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing methylmalonyl-CoA (CHEBI:16625) has functional parent methylmalonic acid (CHEBI:30860)
methylmalonyl-CoA (CHEBI:16625) has role human metabolite (CHEBI:77746)
methylmalonyl-CoA (CHEBI:16625) is a malonyl-CoAs (CHEBI:25136)
methylmalonyl-CoA (CHEBI:16625) is conjugate acid of methylmalonyl-CoA(5−) (CHEBI:59916)
Incoming (R)-methylmalonyl-CoA (CHEBI:15465) is a methylmalonyl-CoA (CHEBI:16625)
(S)-methylmalonyl-CoA (CHEBI:15466) is a methylmalonyl-CoA (CHEBI:16625)
methylmalonyl-CoA(5−) (CHEBI:59916) is conjugate base of methylmalonyl-CoA (CHEBI:16625)
IUPAC Name
3'-phosphoadenosine 5'-[3-(3-hydroxy-2,2-dimethyl-4-{[3-({2-[(2-methyl-3-oxopropanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl) dihydrogen diphosphate]
Synonyms Sources
2-methyl-3-oxopropanoyl-CoAs ChEBI
2-methylmalonyl-CoA ChEBI
2-Methylmalonyl-CoA KEGG COMPOUND
Methylmalonyl coemzyme A KEGG COMPOUND
methylmalonyl coenzyme A ChEBI
Methylmalonyl coenzyme A KEGG COMPOUND
Methylmalonyl-CoA KEGG COMPOUND
Manual Xrefs Databases
C02557 KEGG COMPOUND
HMDB0001269 HMDB
MCA PDBeChem
Methylmalonyl-CoA MetaCyc
Methylmalonyl-CoA Wikipedia
View more database links
Registry Numbers Types Sources
1264-45-5 CAS Registry Number KEGG COMPOUND
1264-45-5 CAS Registry Number ChemIDplus
78364 Reaxys Registry Number Reaxys
Citations Types Sources
24329397 PubMed citation Europe PMC
24568291 PubMed citation Europe PMC
Last Modified
02 February 2015