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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 ester a thioester a coenzyme A-activated compound an acyl-CoA a 2,3,4-saturated fatty acyl CoA a long-chain 2,3,4-saturated fatty acyl CoA
an ester a thioester a coenzyme A-activated compound an acyl-CoA a long-chain acyl-CoA a long-chain 2,3,4-saturated fatty acyl CoA

Component of: FadR-acyl-CoA (summary available)

Chemical Formula: C37H62N7O17P3S

Molecular Weight: 1001.9 Daltons

Monoisotopic Molecular Weight: 1005.3448739507 Daltons

SMILES: CCCCCCCCCCCCCCCC(SCCNC(=O)CCNC(=O)C(O)C(C)(C)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-])=O

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

InChIKey: InChIKey=MNBKLUUYKPBKDU-BBECNAHFSA-J

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 + NADP+ → a trans-2-enoyl-CoA + NADPH + H+
a 2,3,4-saturated fatty acyl CoA[periplasmic space] + H2O[periplasmic space] → a 2,3,4-saturated fatty acid[periplasmic space] + coenzyme A[periplasmic space] + H+[periplasmic space]


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

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]

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


References

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 18.5 on Thu Nov 27, 2014, biocyc11.