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MetaCyc Protein Class: a pimeloyl-[acp] methyl ester

Synonyms: a pimelyl-[acp] methyl ester, a pimeloyl-[acyl-carrier protein] methyl ester

Superclasses: a modified protein an acyl-protein thioester an acyl-[acyl-carrier protein] a saturated acyl-[acp]

a pimeloyl-[acp] methyl ester compound structure

SMILES: COC(=O)CCCCCC(=O)SCCNC(=O)CCNC(C(O)C(C)(C)COP(=O)([O-])OCC(N[an apo-[acyl-carrier protein]])C(=O)[an apo-[acyl-carrier protein]])=O

Reactions known to consume the compound:

8-amino-7-oxononanoate biosynthesis I :
a pimeloyl-[acp] methyl ester + H2O → a pimeloyl-[acp] + methanol + H+

acyl-ACP thioesterase pathway :
an acyl-[acyl-carrier protein] + H2O → a fatty acid + a holo-[acyl-carrier protein] + H+

autoinducer AI-1 biosynthesis :
an acyl-[acyl-carrier protein] + S-adenosyl-L-methionine → a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + an N-acyl-L-homoserine lactone + H+

CDP-diacylglycerol biosynthesis II :
an acyl-[acyl-carrier protein] + sn-glycerol 3-phosphate → a 1-acyl-sn-glycerol 3-phosphate + a holo-[acyl-carrier protein]
an acyl-[acyl-carrier protein] + a 1-acyl-sn-glycerol 3-phosphate → a 1,2-diacyl-sn-glycerol 3-phosphate + a holo-[acyl-carrier protein]

CDP-diacylglycerol biosynthesis III :
an acyl-[acyl-carrier protein] + phosphate → an acyl phosphate + a holo-[acyl-carrier protein]
an acyl-[acyl-carrier protein] + a 1-acyl-sn-glycerol 3-phosphate → a 1,2-diacyl-sn-glycerol 3-phosphate + a holo-[acyl-carrier protein]

ornithine lipid biosynthesis :
a lyso-ornithine lipid + an acyl-[acyl-carrier protein] → an ornithine lipid + a holo-[acyl-carrier protein]

Reactions known to produce the compound:

8-amino-7-oxononanoate biosynthesis I :
a pimeloyl-[acp] methyl ester + NAD+ ← an enoylpimeloyl-[acp] methyl ester + NADH + H+

Not in pathways:
an acyl-[acyl-carrier protein] + NAD+ ← a trans-2-enoyl-[acyl-carrier protein] + NADH + H+

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate

Reactions known to both consume and produce the compound:

Not in pathways:
an acyl-[acyl-carrier protein] + a 2-acyl-1-lyso-phosphatidylethanolamine ↔ a holo-[acyl-carrier protein] + an L-1-phosphatidylethanolamine

In Reactions of unknown directionality:

Not in pathways:
an sn-3-D-galactosyl-sn-2-acylglycerol + an acyl-[acyl-carrier protein] = a holo-[acyl-carrier protein] + a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol
an acyl-[acyl-carrier protein] + a malonyl-[acp] + H+ = a 3-oxoacyl-[acp] + CO2 + a holo-[acyl-carrier protein]

Enzymes inhibited by a pimeloyl-[acp] methyl ester, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: β-ketoacyl-ACP synthase [Comment 1]

Inhibitor (Mechanism unknown) of: acetyl-CoA carboxyltransferase [Davis01a] , 2,3,4-saturated fatty acyl-[acp]:NAD+ oxidoreductase [Heath95, Comment 2]

Inhibitor (Other types) of: β-ketoacyl-ACP synthase [Heath96b, Comment 3]


References

Davis01a: Davis MS, Cronan, Jr. JE (2001). "Inhibition of Escherichia coli acetyl coenzyme A carboxylase by acyl-acyl carrier protein." J Bacteriol. 183(4):1499-503. PMID: 11157970

Heath95: Heath RJ, Rock CO (1995). "Enoyl-acyl carrier protein reductase (fabI) plays a determinant role in completing cycles of fatty acid elongation in Escherichia coli." J Biol Chem 270(44);26538-42. PMID: 7592873

Heath96a: Heath RJ, Rock CO (1996). "Regulation of fatty acid elongation and initiation by acyl-acyl carrier protein in Escherichia coli." J Biol Chem 1996;271(4);1833-6. PMID: 8567624

Heath96b: Heath RJ, Rock CO (1996). "Inhibition of beta-ketoacyl-acyl carrier protein synthase III (FabH) by acyl-acyl carrier protein in Escherichia coli." J Biol Chem 1996;271(18);10996-1000. PMID: 8631920


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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 Fri Mar 27, 2015, biocyc14.