Escherichia coli K-12 substr. MG1655 Compound: palmitoyl-CoA

Synonyms: Palmitoyl-CoA (n-C16:0CoA), hexadecanoyl CoA, palmityl-CoA, palmitoyl coenzyme A, palmitoyl CoA

Superclasses: an estera thioestera coenzyme A-activated compoundan acyl-CoAa 2,3,4-saturated fatty acyl CoAa long-chain 2,3,4-saturated fatty acyl CoA
an estera thioestera coenzyme A-activated compoundan acyl-CoAa long-chain acyl-CoAa long-chain 2,3,4-saturated fatty acyl CoA

Component of: FadR-acyl-CoA

Summary from MetaCyc:
Palmitate (palmitic acid) is one of the most common saturated fatty acids found in animals and plants.

The compound was discovered by Edmond Frémy in 1840 in saponified palm oil, of which it is a major component, and was named "palmitique".

It is the first fatty acid produced during lipogenesis (fatty acid synthesis). In cells palmitate is usually found in the form of palmitoyl-[acp], palmitoyl-CoA or incorporated into lipids.

Chemical Formula: C37H62N7O17P3S

Molecular Weight: 1001.9 Daltons

Monoisotopic Molecular Weight: 1005.3448739507 Daltons

palmitoyl-CoA compound structure


InChI: InChI=1S/C37H66N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h24-26,30-32,36,47-48H,4-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/p-4/t26-,30-,31-,32+,36-/m1/s1


Unification Links: CAS:1763-10-6, ChEBI:57379, HMDB:HMDB01338, IAF1260:34063, KEGG:C00154, MetaboLights:MTBLC57379, PubChem:45266605

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -828.409

Reactions known to consume the compound:

CDP-diacylglycerol biosynthesis I :
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 + sn-glycerol 3-phosphate → a 1-acyl-sn-glycerol 3-phosphate + coenzyme A

fatty acid β-oxidation I :
a 2,3,4-saturated fatty acyl CoA + an oxidized electron-transfer flavoprotein + H+ → a trans-2-enoyl-CoA + a reduced electron-transfer flavoprotein

Not in pathways:
a 2,3,4-saturated fatty acyl CoA[periplasm] + H2O[periplasm] → a 2,3,4-saturated fatty acid[periplasm] + coenzyme A[periplasm] + H+[periplasm]

Not in pathways:
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+

Reactions known to produce the compound:

fatty acid β-oxidation I :
a 2,3,4-saturated fatty acyl CoA + acetyl-CoA ← a 3-oxoacyl-CoA + coenzyme A
a 2,3,4-saturated fatty acid + ATP + coenzyme A → a 2,3,4-saturated fatty acyl CoA + AMP + diphosphate

Not in pathways:
a 2,3,4-saturated fatty acyl CoA + NADP+ ← a trans-2-enoyl-CoA + NADPH + H+

Reactions known to both consume and produce the compound:

Not in pathways:
a 2,3,4-saturated fatty acyl CoA + acetate ↔ a 2,3,4-saturated fatty acid + acetyl-CoA

In Reactions of unknown directionality:

Not in pathways:
FadR + an acyl-CoA = FadR-acyl-CoA

Enzymes inhibited by palmitoyl-CoA, sorted by the type of inhibition, are:

Inhibitor (Noncompetitive) of: glycerol-3-phosphate dehydrogenase [Edgar79] Inhibitor (Mechanism unknown) of: crotonyl-[acyl-carrier-protein] reductase [Bergler96]

This compound has been characterized as an alternative substrate of the following enzymes: acyl-CoA thioesterase, 3-hydroxybenzoyl-CoA thioesterase, acyl-CoA:sn-glycerol-3-phosphate 1-O-acyltransferase, acyl-CoA:1-acyl-sn-glycerol-3-phosphate 2-O-acyltransferase

Transcription Units regulated by related protein FadR-acyl-CoA (1 total):

Transcription-unit diagram


Bergler96: Bergler H, Fuchsbichler S, Hogenauer G, Turnowsky F (1996). "The enoyl-[acyl-carrier-protein] reductase (FabI) of Escherichia coli, which catalyzes a key regulatory step in fatty acid biosynthesis, accepts NADH and NADPH as cofactors and is inhibited by palmitoyl-CoA." Eur J Biochem 242(3);689-94. PMID: 9022698

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

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
Page generated by SRI International Pathway Tools version 19.5 on Sat Nov 28, 2015, BIOCYC13A.