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MetaCyc Compound: palmitate

Synonyms: hexadecanoate (n-C16:0), palmitic acid, hexadecanoate, hexadecanoic acid

Superclasses: an acid all carboxy acids a carboxylate a fatty acid a 2,3,4-saturated fatty acid a saturated fatty acid
an acid all carboxy acids a carboxylate a fatty acid a 2,3,4-saturated fatty acid a straight chain 2,3,4-saturated fatty acid an even numbered straight chain 2,3,4-saturated fatty acid
an acid all carboxy acids a carboxylate a fatty acid a long-chain fatty acid

Summary:
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: C16H31O2

Molecular Weight: 255.42 Daltons

Monoisotopic Molecular Weight: 256.2402302714 Daltons

palmitate compound structure

SMILES: CCCCCCCCCCCCCCCC([O-])=O

InChI: InChI=1S/C16H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16(17)18/h2-15H2,1H3,(H,17,18)/p-1

InChIKey: InChIKey=IPCSVZSSVZVIGE-UHFFFAOYSA-M

Unification Links: CAS:57-10-3 , ChEBI:7896 , ChemSpider:440215 , HMDB:HMDB00220 , IAF1260:34386 , KEGG:C00249 , MetaboLights:MTBLC7896 , PubChem:504166 , Wikipedia:Palmitic_acid

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 256.09268 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

cutin biosynthesis , sporopollenin precursors biosynthesis , suberin monomers biosynthesis :
palmitate + NADPH + oxygen + H+ → 16-hydroxypalmitate + NADP+ + H2O

palmitate biosynthesis II (bacteria and plants) , stearate biosynthesis I (animals and fungi) :
palmitate + ATP + coenzyme A → palmitoyl-CoA + AMP + diphosphate

Not in pathways:
palmitate + hydrogen peroxide + H+ → 1-pentadecene + CO2 + 2 H2O
palmitate + a holo-[acyl-carrier protein] + ATP → a palmitoyl-[acp] + AMP + diphosphate

fatty acid α-oxidation I :
a 2,3,4-saturated fatty acid + oxygen → a 2(R)-hydroperoxy fatty acid

fatty acid β-oxidation (peroxisome, yeast) , fatty acid β-oxidation I , fatty acid β-oxidation II (peroxisome) , fatty acid β-oxidation VI (peroxisome) :
a 2,3,4-saturated fatty acid + ATP + coenzyme A → a 2,3,4-saturated fatty acyl CoA + AMP + diphosphate

alkane biosynthesis I :
a long-chain fatty acid + a holo-[acyl-carrier protein] + ATP → a long-chain acyl-[acp] + AMP + diphosphate

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

sophorolipid biosynthesis :
a long-chain fatty acid + NADPH + oxygen + H+ → an (ω-1)-hydroxy long-chain fatty acid + NADP+ + H2O
a long-chain fatty acid + NADPH + oxygen + H+ → an ω-hydroxy long-chain fatty acid + NADP+ + H2O

terminal olefins biosynthesis I :
a long-chain fatty acid + hydrogen peroxide + H+ → a terminal olefin + CO2 + 2 H2O

alkane oxidation :
a fatty acid + NADPH + oxygen + H+ → an ω-hydroxy fatty acid + NADP+ + H2O

rhizobactin 1021 biosynthesis :
rhizobactin 1021 core + a fatty acid → rhizobactin 1021

saframycin A biosynthesis :
a fatty acid + a holo-[SfmA peptidyl-carrier-protein] + H+ → an acyl-[SfmA peptidyl-carrier-protein] + H2O

Not in pathways:
a fatty acid + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a fatty acid-methyl ester
a fatty acid + a holo-[acyl-carrier protein] + ATP → a 2,3,4-saturated fatty acyl-[acp] + AMP + diphosphate

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

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

cutin biosynthesis , sporopollenin precursors biosynthesis , suberin monomers biosynthesis :
palmitoyl-CoA + H2O → palmitate + coenzyme A + H+

palmitate biosynthesis I (animals and fungi) :
palmitoyl-CoA + H2O → palmitate + coenzyme A + H+
a palmitoyl-[acp] + H2O → palmitate + a holo-[acyl-carrier protein] + H+

palmitate biosynthesis II (bacteria and plants) :
a palmitoyl-[acp] + H2O → palmitate + a holo-[acyl-carrier protein] + H+

phospholipid remodeling (phosphatidylcholine, yeast) :
1,2-dipalmitoyl-phosphatidylcholine + H2O → 1-16:0-2-lysophosphatidylcholine + palmitate + H+

Not in pathways:
a palmitoylated protein + H2O → palmitate + a protein
all-trans-retinyl palmitate + H2O → all-trans-retinol + palmitate + H+
11-cis-retinyl palmitate + H2O → palmitate + 11-cis-retinol + H+
all-trans-retinyl palmitate + H2O → a retinol + palmitate + H+
all-trans-retinyl palmitate + H2O → 11-cis-retinol + palmitate + H+
1-palmitoyl-2-linoleoyl-phosphatidylcholine + H2O → 1-18:2-lysophosphatidylcholine + palmitate + H+

acyl-CoA hydrolysis :
a 2,3,4-saturated fatty acyl CoA + H2O → a 2,3,4-saturated fatty acid + coenzyme A + H+

phosphatidylcholine acyl editing :
a phosphatidylcholine + H2O → a 1-acyl 2-lyso-phosphatidylcholine + a long-chain fatty acid + H+
a phosphatidylcholine + H2O → a 2-acyl 1-lyso-phosphatidylcholine + a long-chain fatty acid + H+

phospholipases :
a phosphatidylcholine + H2O → a 1-acyl 2-lyso-phosphatidylcholine + a long-chain fatty acid + H+
a phosphatidylcholine + H2O → a 2-acyl 1-lyso-phosphatidylcholine + a long-chain fatty acid + H+

retinol biosynthesis :
an all-trans-retinyl ester + H2O → all-trans-retinol + a long-chain fatty acid + H+
a dietary all-trans-retinyl ester + H2O → all-trans-retinol + a long-chain fatty acid + H+

Not in pathways:
a wax ester + H2O → a long-chain alcohol + a long-chain fatty acid + H+
a long-chain-fatty-acyl ethyl ester + H2O → a long-chain fatty acid + ethanol + H+

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

alkane oxidation , fatty acid α-oxidation I :
a fatty aldehyde + NAD+ + H2O → a fatty acid + NADH + 2 H+

ceramide degradation :
a ceramide + H2O → a sphingoid base + a fatty acid

sphingolipid biosynthesis (mammals) , sphingomyelin metabolism :
an N-acyl-sphingosylphosphorylcholine + H2O → a fatty acid + sphingosylphosphorylcholine

sphingosine and sphingosine-1-phosphate metabolism :
a (4E)-sphing-4-enine ceramide + H2O → sphingosine + a fatty acid

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

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
aculeacin A + H2O = a cyclo-hexapeptide + palmitate
palmitaldehyde + NAD+ + H2O = palmitate + NADH + 2 H+
2 hydrogen peroxide + palmitate + H+ = CO2 + pentadecanal + 3 H2O

Not in pathways:
a long-chain acyl-CoA + H2O = a long-chain fatty acid + coenzyme A + H+
an acylglycerone phosphate + a long-chain alcohol = a 1-alkyl-glycerone 3-phosphate + a long-chain fatty acid + H+
a long-chain alcohol + 2 NAD+ + H2O = a long-chain fatty acid + 2 NADH + 3 H+
a long-chain aldehyde + NAD+ + H2O = a long-chain fatty acid + NADH + 2 H+
an N-long-chain-fatty-acyl-L-glutamate + H2O = L-glutamate + a long-chain fatty acid
an N-(long-chain-acyl)ethanolamine + H2O = a long-chain fatty acid + ethanolamine
acetyl-CoA + n malonyl-CoA + 2n NADPH + 2n H+ = a long-chain fatty acid + n CO2 + (n+1) coenzyme A + 2n NADP+

Not in pathways:
a fatty acid + hydrogen peroxide = a 3- or 2-hydroxy fatty acid + H2O
a fatty acid + L-alanine + glycine + a holo-[SfmB peptidyl-carrier-protein] + H+ = an acyl-L-alanyl-glycyl-[SfmB peptidyl-carrier-protein] + 3 H2O
a D-glucosyl-N-acylsphingosine + H2O = a fatty acid + O-glucosyl-sphingosine
a 1,2-diacyl-sn-glycerol + H2O = a 1-monoglyceride + a fatty acid + H+
a glycosphingolipid + H2O = a lyso-glycosphingolipid + a fatty acid

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+

In Transport reactions:
a long-chain fatty acid[periplasmic space]a long-chain fatty acid[cytosol] ,
a long-chain fatty acid[extracellular space]a long-chain fatty acid[periplasmic space]

Enzymes activated by palmitate, sorted by the type of activation, are:

Activator (Allosteric) of: pyruvate oxidase [Kiuchi84]

Activator (Mechanism unknown) of: pantoate:β-alanine ligase [Genschel99] , pyruvate dehydrogenase [Camp88]

This compound has been characterized as an alternative substrate of the following enzymes: fatty-acid peroxygenase , fatty acid (ω-1)-hydroxylase , palmitoyl-CoA 11-desaturase , long-chain acyl-CoA synthetase , alkane ω-hydroxylase


References

Camp88: Camp, Pamela J, Miernyk, Jan A, Randall, Douglas D (1988). "Some kinetic and regulatory properties of the pea chloroplast pyruvate dehydrogenase complex." Biochimica et Biophysica Acta, 933:269-275.

Genschel99: Genschel U, Powell CA, Abell C, Smith AG (1999). "The final step of pantothenate biosynthesis in higher plants: cloning and characterization of pantothenate synthetase from Lotus japonicus and Oryza sativum (rice)." Biochem J 341 ( Pt 3);669-78. PMID: 10417331

Kiuchi84: Kiuchi K, Hager LP (1984). "Reconstitution of the lipid-depleted pyruvate oxidase system of Escherichia coli: the palmitic acid effect." Arch Biochem Biophys 233(2);776-84. PMID: 6385860

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


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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 Wed Jul 29, 2015, biocyc14.