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discounted EARLY registration ends Dec 31, 2014
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discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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 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).

Chemical Formula: C16H31O2

Molecular Weight: 255.42 Daltons

Monoisotopic Molecular Weight: 256.2402302714 Daltons

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

stearate biosynthesis I (animals) :
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 III :
an even numbered straight chain 2,3,4-saturated fatty acid + NAD(P)H + H+ + oxygen → a (R)-2-hydroxy even numbered straight chain 2,3,4-saturated fatty acid + NAD(P)+ + H2O

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

alkane biosynthesis II , fatty acid activation , long chain fatty acid ester synthesis for microdiesel production , phosphatidylcholine acyl editing , wax esters biosynthesis II :
a long-chain fatty acid + ATP + coenzyme A → a long-chain acyl-CoA + AMP + diphosphate

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

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

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

sporopollenin precursor biosynthesis :
a fatty acid + NADPH + oxygen + H+ → an in-chain hydroxy fatty acid + NADP+ + H2O
a fatty acid + NADPH + oxygen + H+ → an ω-hydroxy fatty acid + NADP+ + H2O


ATP + a holo-[acyl-carrier protein] + a fatty acid → AMP + a 2,3,4-saturated fatty acyl-[acp] + diphosphate
a fatty acid + S-adenosyl-L-methionine → S-adenosyl-L-homocysteine + a fatty acid-methyl ester

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


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:

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+

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+


a long-chain-fatty-acyl ethyl ester + H2O → a long-chain fatty acid + ethanol + H+

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

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

phospholipases :
a phosphatidylcholine + H2O → a 2-lyso-phosphatidylcholine + a fatty acid + H+
a phosphatidylcholine + H2O → a 1-lysophosphatidylcholine + a fatty acid + H+

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

sphingosine and sphingosine-1-phosphate metabolism :
an N-acylsphingosine + H2O → sphingosine + a fatty acid

the visual cycle I (vertebrates) :
an all-trans-retinyl ester + H2O → 11-cis-retinol + a fatty acid

triacylglycerol degradation :
a 1-monoglyceride + H2O → a fatty acid + glycerol + H+
a triglyceride + H2O → a 1,2-diglyceride + a fatty acid + H+
a 1,2-diglyceride + H2O → a 2-monoglyceride + a fatty acid + H+


a 3-(acyloxy)acyl group of bacterial toxin + H2O → a 3-hydroxyacyl group of bacterial toxin + a fatty acid + H+
a steryl-ester + H2O → a fatty acid + a sterol + H+
an L-1-phosphatidyl-ethanolamine[periplasmic space] + H2O[periplasmic space] → a 1-lyso-2-acyl-sn-glycero-3-phosphoethanolamine[periplasmic space] + a fatty acid[periplasmic space] + H+[periplasmic space]
a 2-monoglyceride + H2O → glycerol + a fatty acid + H+
an L-1-phosphatidyl-ethanolamine[periplasmic space] + H2O[periplasmic space]a fatty acid[periplasmic space] + a 2-lyso-phosphatidyl-ethanolamine[periplasmic space] + H+[periplasmic space]
a 1,3-diglyceride + H2O → a monoglyceride + a fatty acid
an all-trans-retinyl ester + H2O → 13-cis-retinol + a fatty acid
an 11-cis-retinyl ester + H2O → 11-cis-retinol + a fatty acid
a 1,2-diacyl-sn-glycerol + H2O → a monoglyceride + a fatty acid
an O-acyl-L-carnitine + H2O → L-carnitine + a fatty acid

3,3'-thiodipropionate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropionate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+


an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

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
2 hydrogen peroxide + palmitate + H+ = CO2 + pentadecanal + 3 H2O


acetyl-CoA + n malonyl-CoA + 2n NADPH + 2n H+ = a long-chain fatty acid + n CO2 + (n+1) coenzyme A + 2n NADP+


a fatty acid + hydrogen peroxide = a 3- or 2-hydroxy fatty acid + H2O
a D-glucosyl-N-acylsphingosine + H2O = a fatty acid + D-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


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
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 electron acceptor + H2O = a carboxylate + a reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

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]


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."


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 18.5 on Sun Nov 23, 2014, biocyc13.