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MetaCyc Reaction: 3.1.2.20

Superclasses: Reactions Classified By Conversion TypeSimple ReactionsChemical Reactions
Reactions Classified By SubstrateSmall-Molecule Reactions

EC Number: 3.1.2.20

Enzymes and Genes:

Canis lupus familiaris: acyl-coA hydrolase (long chain)Inferred from experiment: CESdD1
Escherichia coli K-12 substr. MG1655: thioesterase IIInferred from experiment: tesB
acyl-CoA thioesteraseInferred from experiment: yciA

The direction shown, i.e. which substrates are on the left and right sides, is in accordance with the direction in which it was curated.

Most BioCyc compounds have been protonated to a reference pH value of 7.3. Please see the PGDB Concepts Guide for more information.

Mass balance status: Balanced.

Instance reactions:
propanoyl-CoA + H2O → propanoate + coenzyme A + H+ (3.1.2.18)

lauroyl-CoA + H2O → laurate + coenzyme A + H+ (3.1.2.2)

decanoyl-CoA + H2O → decanoate + coenzyme A + H+ (3.1.2.2)

myristoyl-CoA + H2O → myristate + coenzyme A + H+ (3.1.2.2)

3-oxo-myristoyl-CoA + H2O → 3-oxo-myristate + coenzyme A + H+ (3.1.2.-)

icosanoyl-CoA + H2O → arachidate + coenzyme A + H+ (3.1.2.2)

docosapentaenoyl-CoA + H2O → (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentenoate + coenzyme A + H+ (3.1.2.-)

palmitoyl-CoA + H2O → palmitate + coenzyme A + H+ (3.1.2.2)

docosahexaenoyl-CoA + H2O = docosahexaenoate + coenzyme A + H+ (3.1.2.2)

stearoyl-CoA + H2O → stearate + coenzyme A + H+ (3.1.2.2)

(R)-3-hydroxybutanoyl-CoA + H2O → (R)-3-hydroxybutanoate + coenzyme A + H+ (no EC#)

(S)-3-hydroxybutanoyl-CoA + H2O → (S)-3-hydroxybutanoate + coenzyme A + H+ (no EC#)

palmitoleoyl-CoA + H2O → palmitoleate + coenzyme A + H+ (3.1.2.-)

oleoyl-CoA + H2O → oleate + coenzyme A + H+ (3.1.2.2)

a 3-oxoacyl-CoA + H2O → a 3-oxoacid + coenzyme A + H+ (3.1.2.-)

a long-chain acyl-CoA + H2O → a long-chain fatty acid + coenzyme A + H+ (3.1.2.2)

a medium-chain acyl-CoA + H2O → a medium-chain carboxylate + coenzyme A + H+ (3.1.2.19)

a 2,3,4-saturated fatty acyl CoA + H2O → a 2,3,4-saturated fatty acid + coenzyme A + H+ (3.1.2.2)

a short-chain acyl-CoA + H2O → a short-chain carboxylate + coenzyme A + H+ (3.1.2.18)

Enzyme Commission Primary Name: acyl-CoA hydrolase

Enzyme Commission Synonyms: acyl coenzyme A thioesterase, acyl coenzyme A hydrolase, thioesterase B, thioesterase II, acyl-CoA thioesterase

Standard Gibbs Free Energy (ΔrG in kcal/mol): 312.0276Inferred by computational analysis [Latendresse13]

Enzyme Commission Summary:
Broad specificity for medium- to long-chain acyl-CoA. Insensitive to NAD+ (cf. EC 3.1.2.19 ADP-dependent medium-chain-acyl-CoA hydrolase).

Citations: [Alexson89]

Gene-Reaction Schematic

Gene-Reaction Schematic

Instance reactions of [an acyl-CoA + H2O → a carboxylate + coenzyme A + H+] (3.1.2.20):
i1: propanoyl-CoA + H2O → propanoate + coenzyme A + H+ (3.1.2.18)

i2: lauroyl-CoA + H2O → laurate + coenzyme A + H+ (3.1.2.2)

i3: decanoyl-CoA + H2O → decanoate + coenzyme A + H+ (3.1.2.2)

i4: myristoyl-CoA + H2O → myristate + coenzyme A + H+ (3.1.2.2)

i5: 3-oxo-myristoyl-CoA + H2O → 3-oxo-myristate + coenzyme A + H+ (3.1.2.-)

i6: icosanoyl-CoA + H2O → arachidate + coenzyme A + H+ (3.1.2.2)

i7: docosapentaenoyl-CoA + H2O → (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentenoate + coenzyme A + H+ (3.1.2.-)

i8: palmitoyl-CoA + H2O → palmitate + coenzyme A + H+ (3.1.2.2)

i9: docosahexaenoyl-CoA + H2O = docosahexaenoate + coenzyme A + H+ (3.1.2.2)

i10: stearoyl-CoA + H2O → stearate + coenzyme A + H+ (3.1.2.2)

i11: (R)-3-hydroxybutanoyl-CoA + H2O → (R)-3-hydroxybutanoate + coenzyme A + H+ (no EC#)

i12: (S)-3-hydroxybutanoyl-CoA + H2O → (S)-3-hydroxybutanoate + coenzyme A + H+ (no EC#)

i13: palmitoleoyl-CoA + H2O → palmitoleate + coenzyme A + H+ (3.1.2.-)

i14: oleoyl-CoA + H2O → oleate + coenzyme A + H+ (3.1.2.2)

i15: a 3-oxoacyl-CoA + H2O → a 3-oxoacid + coenzyme A + H+ (3.1.2.-)

i16: a long-chain acyl-CoA + H2O → a long-chain fatty acid + coenzyme A + H+ (3.1.2.2)

i17: a medium-chain acyl-CoA + H2O → a medium-chain carboxylate + coenzyme A + H+ (3.1.2.19)

i18: a 2,3,4-saturated fatty acyl CoA + H2O → a 2,3,4-saturated fatty acid + coenzyme A + H+ (3.1.2.2)

i19: a short-chain acyl-CoA + H2O → a short-chain carboxylate + coenzyme A + H+ (3.1.2.18)

Unification Links: KEGG:R00383

Relationship Links: BRENDA:EC:3.1.2.20, ENZYME:EC:3.1.2.20, IUBMB-ExplorEnz:EC:3.1.2.20, Rhea:RELATED-TO:16781, UniProt:RELATED-TO:O00154


References

Alexson89: Alexson SE, Svensson LT, Nedergaard J (1989). "NADH-sensitive propionyl-CoA hydrolase in brown-adipose-tissue mitochondria of the rat." Biochim Biophys Acta 1005(1);13-9. PMID: 2570608

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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