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	ChemicalBook:CB7125746, ChemicalBook:CB2752440, eMolecules:494705, eMolecules:29781161, Selleckchem:Levonorgestrel(Levonelle), ZINC000003814395

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M END): 19 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

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Molfile expand

Wikipedia	License
Levonorgestrel is a hormonal medication which is used in a number of birth control methods. It is combined with an estrogen to make combination birth control pills. As an emergency birth control, sold under the brand names Plan B One-Step and Julie, among others, it is useful within 72 hours of unprotected sex. The more time that has passed since sex, the less effective the medication becomes, and it does not work after pregnancy (implantation) has occurred. Levonorgestrel works by preventing ovulation or fertilization from occurring. It decreases the chances of pregnancy by 57–93%. In an intrauterine device (IUD), such as Mirena among others, it is effective for the long-term prevention of pregnancy. A levonorgestrel-releasing implant is also available in some countries. Common side effects include nausea, breast tenderness, headaches, and increased, decreased, or irregular menstrual bleeding. When used as an emergency contraceptive, if pregnancy occurs, there is no evidence that its use harms the fetus. It is safe to use during breastfeeding. Birth control that contains levonorgestrel will not change the risk of sexually transmitted infections. It is a progestin and has effects similar to those of the hormone progesterone. It works primarily by preventing ovulation and closing off the cervix to prevent the passage of sperm. Levonorgestrel was patented in 1960 and introduced for medical use together with ethinylestradiol in 1970. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In the United States, levonorgestrel-containing emergency contraceptives are available over the counter (OTC) for all ages. In 2020, it was the 323rd most commonly prescribed medication in the United States, with more than 800 thousand prescriptions.
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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	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

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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