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MetaCyc Protein Class: an octanoyl-[acp]

Superclasses: a modified protein an acyl-protein thioester an acyl-[acyl-carrier protein] a 2,3,4-saturated fatty acyl-[acp]
a modified protein an acyl-protein thioester an acyl-[acyl-carrier protein] a saturated acyl-[acp]

an octanoyl-[acp] compound structure

Alternative forms of an octanoyl-[acp]:
a holo-[acyl-carrier protein] (extended summary available)
a 2,3,4-saturated fatty acyl-[acp]
an acyl-[acyl-carrier protein] (summary available)
a (3R)-3-hydroxybutanoyl-[acp]
a (3R)-3-hydroxydodecanoyl-[acp]
a (3R)-3-hydroxyhexanoyl-[acp]
a (3R)-3-hydroxymyristoyl-[acp]
a (3R)-3-hydroxyoctanoyl-[acp]
an acetoacetyl-[acp]
a (3R)-3-hydroxypalmitoyl-[acp]
an arachidoyl-[acp]
a malonyl-[acp]
an acetyl-[acp]

SMILES: CCCCCCCC(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)=O

Unification Links: IAF1260:1446145

Reactions known to consume the compound:

lipoate biosynthesis and incorporation (glycine cleavage system, yeast) , lipoate biosynthesis and incorporation III (Bacillus) :
an octanoyl-[acp] + [glycine cleavage system lipoyl-carrier protein]-L-lysine → a [glycine-cleavage complex H protein] N6-octanoyl-L-lysine + a holo-[acyl-carrier protein] + H+

lipoate biosynthesis and incorporation (pyruvate dehydrogenase and oxoglutarate dehydrogenase, yeast) :
an octanoyl-[acp] + coenzyme A → octanoyl-CoA + a holo-[acyl-carrier protein]

lipoate biosynthesis and incorporation I :
an octanoyl-[acp] + a [lipoyl-carrier protein]-L-lysine → a [lipoyl-carrier protein] N6-octanoyl-L-lysine + a holo-[acyl-carrier protein] + H+

palmitate biosynthesis I (animals and fungi) :
an octanoyl-[acp] + malonyl-CoA + H+ → a 3-oxo-decanoyl-[acp] + CO2 + coenzyme A

palmitate biosynthesis II (bacteria and plants) :
an octanoyl-[acp] + a malonyl-[acp] + H+ → a 3-oxo-decanoyl-[acp] + CO2 + a holo-[acyl-carrier protein]

fatty acid elongation -- saturated :
a 2,3,4-saturated fatty acyl-[acp] + a malonyl-[acp] + H+ → a 3-oxoacyl-[acp] + CO2 + a holo-[acyl-carrier protein]

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:

octanoyl-[acyl-carrier protein] biosynthesis (mitochondria, yeast) :
a 3-oxo-octanoyl-[acp] + 2 NADPH + 2 H+an octanoyl-[acp] + 2 NADP+ + H2O

palmitate biosynthesis I (animals and fungi) :
an octanoyl-[acp] + NADP+ ← a trans oct-2-enoyl-[acp] + NADPH + H+

palmitate biosynthesis II (bacteria and plants) :
an octanoyl-[acp] + NAD+ ← a trans oct-2-enoyl-[acp] + NADH + H+

Not in pathways:
octanoate + a holo-[acyl-carrier protein] + ATP → an octanoyl-[acp] + AMP + diphosphate

fatty acid elongation -- saturated :
a 2,3,4-saturated fatty acyl-[acp] + NAD+ ← a trans-2-enoyl-[acyl-carrier protein] + NADH + H+
a 2,3,4-saturated fatty acyl-[acp] + NADP+ ← a trans-2-enoyl-[acyl-carrier protein] + NADPH + H+

triclosan resistance :
a 2,3,4-saturated fatty acyl-[acp] + NAD+ ← a trans-2-enoyl-[acyl-carrier protein] + NADH + H+

Not in pathways:
a fatty acid + a holo-[acyl-carrier protein] + ATP → a 2,3,4-saturated fatty acyl-[acp] + AMP + diphosphate

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 octanoyl-[acp] + S-adenosyl-L-methionine = a holo-[acyl-carrier protein] + S-methyl-5'-thioadenosine + VAI-1-2 + H+

Not in pathways:
a 2,3,4-saturated fatty acyl-[acp] + a 2,3,4-saturated 2-lysophosphatidate = a 2,3,4-saturated L-phosphatidate + a holo-[acyl-carrier protein]

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

Enzymes inhibited by an octanoyl-[acp], sorted by the type of inhibition, are:

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

Inhibitor (Mechanism unknown) of: acetyl-CoA carboxyltransferase [Davis01] , 2,3,4-saturated fatty acyl-[acp]:NAD+ oxidoreductase [Heath95, Comment 2]

Inhibitor (Other types) of: β-ketoacyl-ACP synthase [Heath96a, Comment 3]

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Instance reactions of [an acyl-carrier protein + coenzyme A → adenosine 3',5'-bisphosphate + a holo-[acyl-carrier protein] + H+] (2.7.8.7):
i1: [EntB aryl-carrier protein] + coenzyme A → a holo-[EntB isochorismatase/aryl-carrier protein] + adenosine 3',5'-bisphosphate + H+ (2.7.8.7)

i2: AsbD acyl-carrier protein + coenzyme A → adenosine 3',5'-bisphosphate + a holo-[AsbD acyl-carrier protein] + H+ (no EC#)


References

Davis01: 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). "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

Heath96b: 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


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 Sat Aug 29, 2015, biocyc11.