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MetaCyc Compound: docosanoyl-CoA

Synonyms: behenoyl CoA

Superclasses: an estera thioestera coenzyme A-activated compoundan acyl-CoAa 2,3,4-saturated fatty acyl CoAa long-chain 2,3,4-saturated fatty acyl CoA
an estera thioestera coenzyme A-activated compoundan acyl-CoAa long-chain acyl-CoAa long-chain 2,3,4-saturated fatty acyl CoA

Summary:
In cells behenate (docosanoate) is usually found in the form of behenoyl-[acp], docosanoyl-CoA or incorporated into lipids.

Citations: [Yang10]

Chemical Formula: C43H74N7O17P3S

Molecular Weight: 1086.1 Daltons

Monoisotopic Molecular Weight: 1089.4387743359 Daltons

docosanoyl-CoA compound structure

SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)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-]

InChI: InChI=1S/C43H78N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/p-4/t32-,36-,37-,38+,42-/m1/s1

InChIKey: InChIKey=NDDZLVOCGALPLR-GNSUAQHMSA-J

Unification Links: ChEBI:65059, PubChem:25201268

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -63.619102Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

suberin monomers biosynthesis :
docosanoyl-CoA + NADPH + oxygen + H+ → 22-hydroxy-docosanoyl-CoA + NADP+ + H2O

very long chain fatty acid biosynthesis II :
docosanoyl-CoA + malonyl-CoA + H+ → 3-oxo-lignoceroyl-CoA + CO2 + coenzyme A

alkane biosynthesis II :
a long-chain aldehyde + coenzyme A + NAD+a long-chain acyl-CoA + NADH + H+

bacterial bioluminescence :
a long-chain acyl-CoA + H2O → a long-chain fatty acid + coenzyme A + H+

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

ceramide de novo biosynthesis :
D-erythro-sphinganine + a long-chain acyl-CoA → a dihydroceramide + coenzyme A + H+

cuticular wax biosynthesis :
a very long chain alcohol + a long-chain acyl-CoA → a wax ester + coenzyme A

diacylglycerol and triacylglycerol biosynthesis :
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

long chain fatty acid ester synthesis for microdiesel production :
a long-chain acyl-CoA + ethanol → a fatty acid-ethyl ester + coenzyme A

sphingolipid biosynthesis (plants) :
D-erythro-sphinganine + a long-chain acyl-CoA → a dihydroceramide + coenzyme A + H+

wax esters biosynthesis I :
a long-chain acyl-CoA + 2 NADPH + 2 H+ → a long-chain alcohol + coenzyme A + 2 NADP+
a long-chain acyl-CoA + a long-chain alcohol → a long-chain ester + coenzyme A

wax esters biosynthesis II :
a long-chain acyl-CoA + a long-chain alcohol → a long-chain ester + coenzyme A
a long-chain aldehyde + coenzyme A + NAD+a long-chain acyl-CoA + NADH + H+

Not in pathways:
a long-chain acyl-CoA + NADPH + oxygen + H+ → an ω-hydroxy fatty acyl-CoA + NADP+ + H2O

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

fatty acid β-oxidation (peroxisome, yeast) , fatty acid β-oxidation II (peroxisome) , fatty acid β-oxidation VI (peroxisome) :
a 2,3,4-saturated fatty acyl CoA + oxygen → a trans-2-enoyl-CoA + hydrogen peroxide

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

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

diacylglycerol and triacylglycerol biosynthesis :
an acyl-CoA + a 1,2-diacyl-sn-glycerol → a triacyl-sn-glycerol + coenzyme A

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

methyl ketone biosynthesis :
an acyl-CoA + oxygen → a trans-2-enoyl-CoA + hydrogen peroxide

phosphatidylcholine biosynthesis VII :
an acyl-CoA + sn-glycero-3-phosphocholine → a 1-acyl 2-lyso-phosphatidylcholine + coenzyme A

Reactions known to produce the compound:

very long chain fatty acid biosynthesis II :
docosanoyl-CoA + NADP+trans-docos-2-enoyl-CoA + NADPH + H+

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

fatty acid β-oxidation (peroxisome, yeast) :
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

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

fatty acid β-oxidation II (peroxisome) :
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

fatty acid β-oxidation VI (peroxisome) :
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

Not in pathways:
a 2,3,4-saturated fatty acyl CoA + NADP+ ← a trans-2-enoyl-CoA + NADPH + H+

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

Not in pathways:
an acyl-CoA + NADP+ ← a 2-enoyl-CoA + NADPH + H+
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate
a 2-oxo carboxylate + 2 an oxidized ferredoxin [iron-sulfur] cluster + coenzyme A → an acyl-CoA + CO2 + 2 a reduced ferredoxin [iron-sulfur] cluster + H+

Reactions known to both consume and produce the compound:

mitochondrial L-carnitine shuttle :
a long-chain acyl-CoA + L-carnitine ↔ an O-acyl-L-carnitine + coenzyme A

Not in pathways:
a 2,3,4-saturated fatty acyl CoA + acetate ↔ a 2,3,4-saturated fatty acid + acetyl-CoA

phosphatidylcholine acyl editing , phosphatidylcholine biosynthesis VII :
an acyl-CoA + a 1-acyl 2-lyso-phosphatidylcholine ↔ a phosphatidylcholine + coenzyme A

Not in pathways:
an acyl-CoA + NAD+ ↔ a trans-2-enoyl-CoA + NADH + H+

In Reactions of unknown directionality:

Not in pathways:
docosanoyl-CoA + sn-glycerol 3-phosphate = 2-docosanoyl-glycerol 3-phosphate + coenzyme A

Not in pathways:
a long-chain 2,3,4-saturated fatty acyl CoA + an oxidized electron-transfer flavoprotein + H+ = a long-chain trans-2,3-dehydroacyl-CoA + a reduced electron-transfer flavoprotein

fatty acids biosynthesis (yeast) :
acetyl-CoA + n malonyl-CoA + 2n NADPH + 4n H+ = a long-chain acyl-CoA + n CO2 + n coenzyme A + 2n NADP+

Not in pathways:
a long-chain acyl-CoA + n malonyl-CoA = a very long chain fatty acyl-CoA + n CO2 + n coenzyme A
a long-chain acyl-CoA + glycerone phosphate = an acylglycerone phosphate + coenzyme A
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 aldehyde + coenzyme A + NADP+ = a long-chain acyl-CoA + NADPH + H+

Not in pathways:
an acyl-CoA + glycine = an N-acylglycine + coenzyme A
a 2-acyl 1-lyso-phosphatidylcholine + an acyl-CoA = a phosphatidylcholine + coenzyme A
a 2-monoglyceride + an acyl-CoA = a 1,2-diacyl-sn-glycerol + coenzyme A
an acyl-CoA + 1-O-alkyl-2-acetyl-sn-glycerol = a 1-O-alkyl-2-acetyl-3-acyl-sn-glycerol + coenzyme A
an acyl-CoA + a 1-alkenylglycerophosphoethanolamine = an O-1-alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + coenzyme A
an acyl-CoA + cholesterol = a cholesterol ester + coenzyme A
an acyl-CoA + pseudotropine = an O-acylpseudotropine + coenzyme A + H+
an acyl-CoA + a 1-alkyl-2-lyso-sn-glycero-3-phosphocholine = a 1-organyl-2-acyl-sn-glycero-3-phosphocholine + coenzyme A
an acyl-CoA + NADP+ = a cis-2-enoyl-CoA + NADPH + H+
an acyl-CoA + sn-glycerol 3-phosphate = a 2-acyl-sn-glycerol 3-phosphate + coenzyme A
an acyl-CoA + tropine = an O-acyltropine + coenzyme A + H+
an acyl-CoA + L-glutamine = an N-acyl-L-glutamine + coenzyme A
an acyl-CoA + a 2-acyl-sn-glycerol 3-phosphate = a 1,2-diacyl-sn-glycerol 3-phosphate + coenzyme A
a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + an acyl-CoA = an L-1-phosphatidyl-inositol + coenzyme A
an acyl-CoA + a 1-O-(alk-1-enyl)glycero-3-phosphocholine = a plasmenylcholine + coenzyme A
an acyl-CoA + a sphingoid base = a ceramide + coenzyme A + H+
all-trans-retinol + an acyl-CoA = an all-trans-retinyl ester + coenzyme A
an acyl-CoA + 2 a ferrocytochrome b5 + oxygen + 2 H+ = an (11E)-enoyl-CoA + 2 a ferricytochrome b5 + 2 H2O
an acyl-CoA + n (R)-methylmalonyl-CoA + 2n NADPH + 2n H+ = a multi-methyl-branched acyl-CoA + n CO2 + n coenzyme A + 2n NADP+ + n H2O

In Transport reactions:
a long-chain acyl-CoA[peroxisomal membrane] + ATP + H2O ↔ a long-chain acyl-CoA[peroxisomal membrane] + ADP + phosphate + H+

Enzymes inhibited by docosanoyl-CoA, sorted by the type of inhibition, are:

Inhibitor (Mechanism unknown) of: glycerol-3-phosphate dehydrogenase [Edgar79], 4-hydroxybenzoate-polyprenyltransferase [Kawahara91]

References

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

Kawahara91: Kawahara, K., Koizumi, N., Kawaji, H., Oishi, K., Uchida, K. (1991). "Partial Purification and Characterization of 4-Hydroxybenzoate-polyprenyltransferase in Ubiquinone Biosynthesis of Pseudomonas putida." Agricultural and biological chemistry 55(9):2307-2311.

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

Yang10: Yang W, Pollard M, Li-Beisson Y, Beisson F, Feig M, Ohlrogge J (2010). "A distinct type of glycerol-3-phosphate acyltransferase with sn-2 preference and phosphatase activity producing 2-monoacylglycerol." Proc Natl Acad Sci U S A 107(26);12040-5. PMID: 20551224


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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
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