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MetaCyc Compound Class: a long-chain acyl-CoA

Synonyms: a fatty acyl-CoA, fatty acyl CoA-, acyl-CoA, a fatty acyl CoA, long-chain acyl-CoA

Superclasses: an ester a thioester a coenzyme A-activated compound an acyl-CoA

Summary:
Acyl-CoAs are oxoacids that have been activated by coenzyme A. They are often classified by the length of their acyl moiety.

Medium-chain acyl-CoAs are derived from fatty acids with aliphatic chains of 6-12 carbons.

Long-chain acyl-CoAs are derived from fatty acids with aliphatic chains of 13-22 carbons.

Very-long-chain fatty acyl-CoAs are derived from fatty acids with aliphatic chains of 23 carbons or longer.

a long-chain acyl-CoA compound structure

Child Classes: a hexadecenoyl-CoA (n-C16:1CoA) (0) , a long-chain 2,3,4-saturated fatty acyl CoA (10) , a [glycerolipid]-(9Z,12Z)-hexadeca-9,12-dienoate (0) , an ω-hydroxy long-chain fatty acyl-CoA (6)

Instances:
(4Z,7Z,10Z,13Z,16Z)-docosapentaenoyl-CoA ,
(9Z,12E)-hexadecadienoyl-CoA ,
(9Z,12Z)-hexadeca-9,12-dienoate ,
(9Z,12Z)-hexadeca-9,12-dienoyl-CoA ,
(9Z,12Z,15Z)-hexadeca-9,12,15-trienoyl-CoA ,
3-oxo adrenoyl-CoA ,
3R-hydroxy-adrenoyl-CoA ,
16-hydroxypalmitoyl-CoA ,
22-carboxy-docosanoyl-CoA ,
22-hydroxy-docosanoyl-CoA ,
adrenoyl-CoA ,
docosapentaenoyl-CoA ,
hexadecanedioyl-CoA ,
ricinoleoyl-CoA

Citations: [Lubert]

SMILES: CC(C)(C(O)C(=O)NCCC(=O)NCCSC(=O)[R])COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-]

Unification Links: ChEBI:33184 , KEGG:C02843

Reactions known to consume the compound:

alkane biosynthesis II :
a long-chain aldehyde + coenzyme A + NAD+a long-chain acyl-CoA + NADH + H+

CDP-diacylglycerol biosynthesis I :
a long-chain acyl-CoA + sn-glycerol 3-phosphate → a 1-acyl-sn-glycerol 3-phosphate + coenzyme A
a long-chain acyl-CoA + a 1-acyl-sn-glycerol 3-phosphate → a 1,2-diacyl-sn-glycerol 3-phosphate + coenzyme A

ceramide de novo biosynthesis :
sphinganine + a long-chain acyl-CoA → a dihydroceramide + coenzyme A + H+

cuticular wax biosynthesis :
a very long chain alcohol + a long-chain acyl-CoA → a wax ester + coenzyme A

diacylglycerol and triacylglycerol biosynthesis :
a long-chain acyl-CoA + sn-glycerol 3-phosphate → a 1-acyl-sn-glycerol 3-phosphate + coenzyme A
a long-chain acyl-CoA + a 1-acyl-sn-glycerol 3-phosphate → a 1,2-diacyl-sn-glycerol 3-phosphate + coenzyme A

long chain fatty acid ester synthesis for microdiesel production :
a long-chain acyl-CoA + ethanol → a fatty acid-ethyl ester + coenzyme A

sphingolipid biosynthesis (plants) :
sphinganine + a long-chain acyl-CoA → a dihydroceramide + coenzyme A + H+

wax esters biosynthesis I :
a long-chain acyl-CoA + a long-chain alcohol → a long-chain ester + coenzyme A
a long-chain acyl-CoA + 2 NADPH + 2 H+ → a long-chain alcohol + coenzyme A + 2 NADP+

wax esters biosynthesis II :
a long-chain aldehyde + coenzyme A + NAD+a long-chain acyl-CoA + NADH + H+
a long-chain acyl-CoA + a long-chain alcohol → a long-chain ester + coenzyme A

Not in pathways:
a long-chain acyl-CoA + NADPH + oxygen + H+ → an ω-hydroxy fatty acyl-CoA + NADP+ + H2O

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

diacylglycerol and triacylglycerol biosynthesis :
an acyl-CoA + a 1,2-diacyl-sn-glycerol → a triacyl-sn-glycerol + coenzyme A

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

methyl ketone biosynthesis :
an acyl-CoA + oxygen → a trans-2-enoyl-CoA + hydrogen peroxide

phosphatidylcholine biosynthesis VII :
an acyl-CoA + sn-glycero-3-phosphocholine → a 1-acyl 2-lyso-phosphatidylcholine + coenzyme A

Not in pathways:
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an acyl-CoA + 2 a ferrocytochrome b5 + oxygen + 2 H+ → a cis Δ11 acyl-CoA + 2 a ferricytochrome b5 + 2 H2O

Reactions known to produce the compound:

alkane biosynthesis II , long chain fatty acid ester synthesis for microdiesel production , long-chain fatty acid activation , phosphatidylcholine acyl editing , wax esters biosynthesis II :
a long-chain fatty acid + ATP + coenzyme A → a long-chain acyl-CoA + AMP + diphosphate

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-CoA + NADP+ ← a 2-enoyl-CoA + NADPH + H+
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to both consume and produce the compound:

mitochondrial L-carnitine shuttle :
a long-chain acyl-CoA + L-carnitine ↔ an O-acyl-L-carnitine + coenzyme A

phosphatidylcholine acyl editing , phosphatidylcholine biosynthesis VII :
an acyl-CoA + a 1-acyl 2-lyso-phosphatidylcholine ↔ a phosphatidylcholine + coenzyme A

Not in pathways:
an acyl-CoA + NAD+ ↔ a trans-2-enoyl-CoA + NADH + H+

In Reactions of unknown directionality:

fatty acids biosynthesis (yeast) :
acetyl-CoA + n malonyl-CoA + 2n NADPH + 4n H+ = a long-chain acyl-CoA + n CO2 + n coenzyme A + 2n NADP+

Not in pathways:
a long-chain aldehyde + coenzyme A + NADP+ = a long-chain acyl-CoA + NADPH + H+
a long-chain acyl-CoA + H2O = a long-chain fatty acid + coenzyme A + H+
a long-chain acyl-CoA + a 1-acyl-sn-glycerol 3-phosphate = a 1,2-diacyl-sn-glycerol 3-phosphate + coenzyme A
a long-chain acyl-CoA + glycerone phosphate = an acylglycerone phosphate + coenzyme A
a long-chain acyl-CoA + n malonyl-CoA = a very long chain fatty acyl-CoA + n CO2 + n coenzyme A

Not in pathways:
an acyl-CoA + n (R)-methylmalonyl-CoA + 2n NADPH + 2n H+ = a multi-methyl-branched acyl-CoA + n CO2 + n coenzyme A + 2n NADP+
an acyl-CoA + glycine = an N-acylglycine + coenzyme A
a 2-acyl 1-lyso-phosphatidylcholine + an acyl-CoA = a phosphatidylcholine + coenzyme A
a 2-monoglyceride + an acyl-CoA = a 1,2-diacyl-sn-glycerol + coenzyme A
an acyl-CoA + 1-O-alkyl-2-acetyl-sn-glycerol = a 1-O-alkyl-2-acetyl-3-acyl-sn-glycerol + coenzyme A
an acyl-CoA + a 1-alkenylglycerophosphoethanolamine = an O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + coenzyme A
an acyl-CoA + cholesterol = a cholesterol ester + coenzyme A
an acyl-CoA + pseudotropine = an O-acylpseudotropine + coenzyme A + H+
an acyl-CoA + a 1-alkyl-2-lyso-sn-glycero-3-phosphocholine = a 1-organyl-2-acyl-sn-glycero-3-phosphocholine + coenzyme A
an acyl-CoA + NADP+ = a cis-2-enoyl-CoA + NADPH + H+
an acyl-CoA + sn-glycerol 3-phosphate = a 2-acyl-sn-glycerol 3-phosphate + coenzyme A
an acyl-CoA + tropine = an O-acyltropine + coenzyme A + H+
an acyl-CoA + L-glutamine = an N-acyl-L-glutamine + coenzyme A
an acyl-CoA + a 2-acyl-sn-glycerol 3-phosphate = a 1,2-diacyl-sn-glycerol 3-phosphate + coenzyme A
a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + an acyl-CoA = an L-1-phosphatidyl-inositol + coenzyme A
an acyl-CoA + a 1-O-(alk-1-enyl)glycero-3-phosphocholine = a plasmenylcholine + coenzyme A
an acyl-CoA + a sphingoid base = a ceramide + coenzyme A + H+
all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + coenzyme A
an acyl-CoA + 2 a ferrocytochrome b5 + oxygen + 2 H+ = a trans Δ11 acyl-CoA + 2 a ferricytochrome b5 + 2 H2O
a 2-oxo carboxylate + 2 an oxidized ferredoxin + coenzyme A = an acyl-CoA + CO2 + 2 a reduced ferredoxin + H+

In Transport reactions:
a long-chain acyl-CoA[peroxisomal membrane] + ATP + H2O ↔ a long-chain acyl-CoA[peroxisomal membrane] + ADP + phosphate + H+

Enzymes inhibited by a long-chain acyl-CoA, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: glycerol-3-phosphate dehydrogenase [Edgar79] , 4-hydroxybenzoate-polyprenyltransferase [Kawahara91]

Credits:
Imported from EcoCyc 19-Sep-2012 by Paley S , SRI International
Revised 19-Oct-2012 by Caspi R , SRI International


References

Edgar79: Edgar JR, Bell RM (1979). "Biosynthesis in Escherichia coli of sn-glycerol 3-phosphate, a precursor of phospholipid. Palmitoyl-CoA inhibition of the biosynthetic sn-glycerol-3-phosphate dehydrogenase." J Biol Chem 1979;254(4);1016-21. PMID: 368067

Kawahara91: Kawahara, K., Koizumi, N., Kawaji, H., Oishi, K., Uchida, K. (1991). "Partial Purification and Characterization of 4-Hydroxybenzoate-polyprenyltransferase in Ubiquinone Biosynthesis of Pseudomonas putida." Agricultural and biological chemistry 55(9):2307-2311.

Lubert: Lubert Stryer "Biochemistry." ISBN 0-7167-1226-1.


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
Page generated by SRI International Pathway Tools version 19.0 on Tue Sep 1, 2015, BIOCYC14B.