coenzyme A (CHEBI:15346)

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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

Supplier Information	ZINC000008551087

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M END): 21 ms

reading 84 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

84 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Coenzyme A (CoA, SHCoA, CoASH) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. All genomes sequenced to date encode enzymes that use coenzyme A as a substrate, and around 4% of cellular enzymes use it (or a thioester) as a substrate. In humans, CoA biosynthesis requires cysteine, pantothenate (vitamin B5), and adenosine triphosphate (ATP). In its acetyl form, coenzyme A is a highly versatile molecule, serving metabolic functions in both the anabolic and catabolic pathways. Acetyl-CoA is utilised in the post-translational regulation and allosteric regulation of pyruvate dehydrogenase and carboxylase to maintain and support the partition of pyruvate synthesis and degradation.
Read full article at Wikipedia

Formula

C21H36N7O16P3S

Net Charge

Average Mass

767.53540

Monoisotopic Mass

767.11521

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: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). 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 3'-phosphate-adenosine-5'-diphosphate (CHEBI:44672) 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 6-aminopurines (CHEBI:20706) coenzyme A (CHEBI:15346) is a nucleotide derivative (CHEBI:231540) coenzyme A (CHEBI:15346) is a secondary carboxamide (CHEBI:140325) coenzyme A (CHEBI:15346) is a thiol (CHEBI:29256) 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,6-cis)-dodeca-2,6-dienoyl-CoA (CHEBI:28387) has functional parent coenzyme A (CHEBI:15346) (2E,4Z)-deca-2,4-dienoyl-CoA (CHEBI:29119) 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) S-nitroso-coenzyme A (CHEBI:229721) 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) malonyl-CoA lithium salt (CHEBI:232859) 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) n-propionyl-CoA lithium salt (CHEBI:233091) 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

Manual Xrefs	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

Last Modified

06 June 2024

General Comment
2024-06-03	Coenzyme 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.

CHEBI:15346 - coenzyme A

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