CHEBI:15346 - coenzyme A

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ChEBI Name coenzyme A
ChEBI ID CHEBI:15346
Definition A thiol comprising a panthothenate unit in phosphoric anhydride linkage with a 3',5'-adenosine diphosphate unit; and an aminoethanethiol unit.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:741566, CHEBI:41631, CHEBI:41597, CHEBI:3771, CHEBI:13294, CHEBI:13295, CHEBI:13298, CHEBI:23355
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Formula C21H36N7O16P3S
Net Charge 0
Average Mass 767.53540
Monoisotopic Mass 767.115
InChI InChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16+,20-/m1/s1
InChIKey RGJOEKWQDUBAIZ-IBOSZNHHSA-N
SMILES CC(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)[C@@H](O)C(=O)NCCC(=O)NCCS
Metabolite of Species Details
Mus musculus (NCBI:10090) Source: BioModels - MODEL1507180067 See: PubMed
Escherichia coli (NCBI:562) 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).
coenzyme
A low-molecular-weight, non-protein organic compound participating in enzymatic reactions as dissociable acceptor or donor of chemical groups or electrons.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing coenzyme A (CHEBI:15346) has functional parent ADP (CHEBI:16761)
coenzyme A (CHEBI:15346) has role Escherichia coli metabolite (CHEBI:76971)
coenzyme A (CHEBI:15346) has role coenzyme (CHEBI:23354)
coenzyme A (CHEBI:15346) has role mouse metabolite (CHEBI:75771)
coenzyme A (CHEBI:15346) is a adenosine 3',5'-bisphosphate (CHEBI:37240)
coenzyme A (CHEBI:15346) is conjugate acid of coenzyme A(4−) (CHEBI:57287)
Incoming γ-butyrobetainyl-CoA (CHEBI:61517) has functional parent coenzyme A (CHEBI:15346)
(1-hydroxycyclohexyl)acetyl-CoA (CHEBI:15448) has functional parent coenzyme A (CHEBI:15346)
(2,3,3-trimethyl-5-oxocyclopent-3-enyl)acetyl-CoA (CHEBI:27866) has functional parent coenzyme A (CHEBI:15346)
(2-trans,4-cis)-deca-2,4-dienoyl-CoA (CHEBI:29119) has functional parent coenzyme A (CHEBI:15346)
(2-trans,6-cis)-dodeca-2,6-dienoyl-CoA (CHEBI:28387) has functional parent coenzyme A (CHEBI:15346)
(3S)-citryl-CoA (CHEBI:15459) has functional parent coenzyme A (CHEBI:15346)
(3Z,6Z)-dodecadienoyl-CoA (CHEBI:28002) has functional parent coenzyme A (CHEBI:15346)
(E)-4-(trimethylammonio)but-2-enoyl-CoA (CHEBI:61123) has functional parent coenzyme A (CHEBI:15346)
(E,E)-piperonyl-CoA (CHEBI:15464) has functional parent coenzyme A (CHEBI:15346)
(R)-methylmalonyl-CoA (CHEBI:15465) has functional parent coenzyme A (CHEBI:15346)
(R)-phenyllactoyl-CoA (CHEBI:11010) has functional parent coenzyme A (CHEBI:15346)
(S)-3-hydroxyhexanoyl-CoA (CHEBI:28276) has functional parent coenzyme A (CHEBI:15346)
(S)-methylmalonyl-CoA (CHEBI:15466) has functional parent coenzyme A (CHEBI:15346)
2'-(5''-phosphoribosyl)-3'-dephospho-CoA (CHEBI:65338) has functional parent coenzyme A (CHEBI:15346)
2'-(5-triphosphoribosyl)-3'-dephospho-CoA (CHEBI:11392) has functional parent coenzyme A (CHEBI:15346)
2-amino-5-oxocyclohex-1-enecarbonyl-CoA (CHEBI:18206) has functional parent coenzyme A (CHEBI:15346)
2-benzylsuccinyl-CoA (CHEBI:22746) has functional parent coenzyme A (CHEBI:15346)
2-furoyl-CoA (CHEBI:15474) has functional parent coenzyme A (CHEBI:15346)
2-methylbutanoyl-CoA (CHEBI:15477) has functional parent coenzyme A (CHEBI:15346)
3'-dephospho-CoA (CHEBI:15468) has functional parent coenzyme A (CHEBI:15346)
3,4,4-trimethylhepta-2,5-dienoyl-CoA (CHEBI:23608) has functional parent coenzyme A (CHEBI:15346)
3,4-dihydro-7-methoxy-2-methylene-3-oxo-2H-1,4-benzoxazine-5-carbonyl-CoA (CHEBI:1373) has functional parent coenzyme A (CHEBI:15346)
3-(4-methylpent-3-en-1-yl)pent-2-enedioyl-CoA (CHEBI:15480) has functional parent coenzyme A (CHEBI:15346)
3-hydroxy-3-(4-methylpent-3-en-1-yl)glutaryl-CoA (CHEBI:15483) has functional parent coenzyme A (CHEBI:15346)
3-hydroxy-3-methylbutyl-CoA (CHEBI:27874) has functional parent coenzyme A (CHEBI:15346)
3-isopropenylpimeloyl-CoA (CHEBI:37439) has functional parent coenzyme A (CHEBI:15346)
3-methylbut-3-enoyl-CoA (CHEBI:28188) has functional parent coenzyme A (CHEBI:15346)
3-oxooctadecanoyl-CoA (CHEBI:50571) has functional parent coenzyme A (CHEBI:15346)
4,8,12-trimethyltridecanoyl-CoA (CHEBI:15495) has functional parent coenzyme A (CHEBI:15346)
5-hydroxythiophene-2-carbonyl-CoA (CHEBI:15502) has functional parent coenzyme A (CHEBI:15346)
6-hydroxycyclohex-1-ene-1-carbonyl-CoA (CHEBI:15505) has functional parent coenzyme A (CHEBI:15346)
6-hydroxyhex-3-enoyl-CoA (CHEBI:49281) has functional parent coenzyme A (CHEBI:15346)
6-oxocyclohex-1-ene-1-carbonyl-CoA (CHEBI:28168) has functional parent coenzyme A (CHEBI:15346)
cis-dodec-3-enoyl-CoA (CHEBI:27989) has functional parent coenzyme A (CHEBI:15346)
cis-geranoyl-CoA (CHEBI:15523) has functional parent coenzyme A (CHEBI:15346)
cis-tetradec-11-enoyl-CoA (CHEBI:15461) has functional parent coenzyme A (CHEBI:15346)
cis-tetradec-3-enoyl-CoA (CHEBI:62014) has functional parent coenzyme A (CHEBI:15346)
N-methylanthraniloyl-CoA (CHEBI:30305) has functional parent coenzyme A (CHEBI:15346)
O3-(phosphoribosyl dephospho-CoA)-L-serine (CHEBI:21979) has functional parent coenzyme A (CHEBI:15346)
S-alkyl-CoA (CHEBI:62204) has functional parent coenzyme A (CHEBI:15346)
trans-3-methylglutaconyl-CoA (CHEBI:15488) has functional parent coenzyme A (CHEBI:15346)
trans-4-carboxybut-2-enoyl-CoA (CHEBI:15497) has functional parent coenzyme A (CHEBI:15346)
trans-dec-2-enoyl-CoA (CHEBI:10723) has functional parent coenzyme A (CHEBI:15346)
trans-dodec-2-enoyl-CoA (CHEBI:15471) has functional parent coenzyme A (CHEBI:15346)
trans-feruloyl-CoA (CHEBI:15511) has functional parent coenzyme A (CHEBI:15346)
trans-hex-2-enoyl-CoA (CHEBI:28706) has functional parent coenzyme A (CHEBI:15346)
trans-oct-2-enoyl-CoA (CHEBI:27537) has functional parent coenzyme A (CHEBI:15346)
trans-tetradec-11-enoyl-CoA (CHEBI:15460) has functional parent coenzyme A (CHEBI:15346)
trans-tetradec-2-enoyl-CoA (CHEBI:27721) has functional parent coenzyme A (CHEBI:15346)
acetyl-CoA (CHEBI:15351) has functional parent coenzyme A (CHEBI:15346)
acryloyl-CoA (CHEBI:15513) has functional parent coenzyme A (CHEBI:15346)
acyl-CoA (CHEBI:17984) has functional parent coenzyme A (CHEBI:15346)
alk-2-enoyl-CoA (CHEBI:15469) has functional parent coenzyme A (CHEBI:15346)
but-2-enoyl-CoA (CHEBI:36926) has functional parent coenzyme A (CHEBI:15346)
butyryl-CoA (CHEBI:15517) has functional parent coenzyme A (CHEBI:15346)
cinnamoyl-CoA (CHEBI:15463) has functional parent coenzyme A (CHEBI:15346)
citramalyl-CoA (CHEBI:15457) has functional parent coenzyme A (CHEBI:15346)
CoA-glutathione (CHEBI:17586) has functional parent coenzyme A (CHEBI:15346)
cyclohexa-1,4-diene-1-carbonyl-CoA (CHEBI:28443) has functional parent coenzyme A (CHEBI:15346)
cyclohexa-1,5-diene-1-carbonyl-CoA (CHEBI:15520) has functional parent coenzyme A (CHEBI:15346)
cyclohexa-2,5-diene-1-carbonyl-CoA (CHEBI:27610) has functional parent coenzyme A (CHEBI:15346)
decanoyl-CoA (CHEBI:28493) has functional parent coenzyme A (CHEBI:15346)
deoxycholoyl-CoA (CHEBI:50111) has functional parent coenzyme A (CHEBI:15346)
farnesoyl-CoA (CHEBI:28562) has functional parent coenzyme A (CHEBI:15346)
feruloyl-CoA (CHEBI:14261) has functional parent coenzyme A (CHEBI:15346)
glutaryl-CoA (CHEBI:15524) has functional parent coenzyme A (CHEBI:15346)
heptanoyl-CoA (CHEBI:37283) has functional parent coenzyme A (CHEBI:15346)
hexanoyl-CoA (CHEBI:27540) has functional parent coenzyme A (CHEBI:15346)
icosanoyl-CoA (CHEBI:15527) has functional parent coenzyme A (CHEBI:15346)
indol-3-ylacetyl-CoA (CHEBI:12755) has functional parent coenzyme A (CHEBI:15346)
isobutyryl-CoA (CHEBI:15479) has functional parent coenzyme A (CHEBI:15346)
itaconyl-CoA (CHEBI:15528) has functional parent coenzyme A (CHEBI:15346)
linoleoyl-CoA (CHEBI:15530) has functional parent coenzyme A (CHEBI:15346)
malonyl-CoA (CHEBI:15531) has functional parent coenzyme A (CHEBI:15346)
methacrylyl-CoA (CHEBI:27754) has functional parent coenzyme A (CHEBI:15346)
myristoyl-CoA (CHEBI:15532) has functional parent coenzyme A (CHEBI:15346)
nonanoyl-CoA (CHEBI:27770) has functional parent coenzyme A (CHEBI:15346)
oleoyl-CoA (CHEBI:15534) has functional parent coenzyme A (CHEBI:15346)
palmitoyl-CoA (CHEBI:15525) has functional parent coenzyme A (CHEBI:15346)
pent-2-enoyl-CoA (CHEBI:27962) has functional parent coenzyme A (CHEBI:15346)
pentanoyl-CoA (CHEBI:15536) has functional parent coenzyme A (CHEBI:15346)
phenylglyoxylyl-CoA (CHEBI:50117) has functional parent coenzyme A (CHEBI:15346)
phytanoyl-CoA (CHEBI:15538) has functional parent coenzyme A (CHEBI:15346)
pimeloyl-CoA (CHEBI:15504) has functional parent coenzyme A (CHEBI:15346)
propionyl-CoA (CHEBI:15539) has functional parent coenzyme A (CHEBI:15346)
sinapoyl-CoA (CHEBI:15540) has functional parent coenzyme A (CHEBI:15346)
succinyl-CoA (CHEBI:15380) has functional parent coenzyme A (CHEBI:15346)
sulfoacetyl-CoA (CHEBI:61992) has functional parent coenzyme A (CHEBI:15346)
tetracosanoyl-CoA (CHEBI:52974) has functional parent coenzyme A (CHEBI:15346)
tetradecenoyl-CoA (CHEBI:26900) has functional parent coenzyme A (CHEBI:15346)
thiophene-2-carbonyl-CoA (CHEBI:15542) has functional parent coenzyme A (CHEBI:15346)
vinylacetyl-CoA (CHEBI:15543) has functional parent coenzyme A (CHEBI:15346)
coenzyme A(4−) (CHEBI:57287) is conjugate base of coenzyme A (CHEBI:15346)
IUPAC Name
3'-phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl] dihydrogen diphosphate}
Synonyms Sources
3'-phosphoadenosine-(5')diphospho(4')pantatheine ChEBI
[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl (3R)-3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphate ChEBI
CoA KEGG COMPOUND
CoA-SH KEGG COMPOUND
CoASH ChEBI
Coenzym A ChEBI
Coenzyme A KEGG COMPOUND
COENZYME A PDBeChem
HSCoA ChEBI
Koenzym A ChEBI
Database Links Databases
C00007258 KNApSAcK
C00010 KEGG COMPOUND
COA PDBeChem
Coenzyme_A Wikipedia
COZ PDBeChem
DB01992 DrugBank
View more database links
Registry Numbers Types Sources
77809 Beilstein Registry Number Beilstein
85-61-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11923312 PubMed citation Europe PMC
13025483 PubMed citation Europe PMC
15014152 PubMed citation Europe PMC
15893380 PubMed citation Europe PMC
18407920 PubMed citation Europe PMC
19666462 PubMed citation Europe PMC
20351285 PubMed citation Europe PMC
2981478 PubMed citation Europe PMC
7310833 PubMed citation ChEMBL
Last Modified
27 January 2016
General Comment
2011-07-22 Coenzyne A is a universal carrier of acyl groups, notable for its rôle in the synthesis and oxidation of fatty acids and the oxidation of pyruvate in the citric (tricarboxylic) acid cycle.