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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound: docosanoyl-CoA

Synonyms: behenoyl CoA

Superclasses: an ester a thioester a coenzyme A-activated compound an acyl-CoA a 2,3,4-saturated fatty acyl CoA a long-chain 2,3,4-saturated fatty acyl CoA
an ester a thioester a coenzyme A-activated compound an acyl-CoA a long-chain acyl-CoA a long-chain 2,3,4-saturated fatty acyl CoA

Citations: [Yang10a]

Chemical Formula: C43H74N7O17P3S

Molecular Weight: 1086.1 Daltons

Monoisotopic Molecular Weight: 1089.4387743359 Daltons

SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OCC1(C(OP(=O)([O-])[O-])C(O)C(O1)N3(C=NC2(C(N)=NC=NC=23))))=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 Change Formation (ΔfG in kcal/mol): -63.619102 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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+

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 :
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

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) :
sphinganine + a long-chain acyl-CoA → a dihydroceramide + coenzyme A + H+

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

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+

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

dimethylsulfoniopropionate 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 2-lyso-phosphatidylcholine + coenzyme A

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

Not in pathways:
an acyl-CoA + a reduced electron acceptor + oxygen → a Δ11 acyl-CoA + an oxidized electron acceptor + 2 H2O
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+

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 , 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

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

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

Not in pathways:
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

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 2-lyso-phosphatidylcholine ↔ a phosphatidylcholine + coenzyme A


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


a long-chain 2,3,4-saturated fatty acyl CoA + an oxidized electron-transfer flavoprotein = 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+


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 + dihydroxyacetone phosphate = an acylglycerone phosphate + coenzyme A
a long-chain aldehyde + coenzyme A + NADP+ = a long-chain acyl-CoA + NADPH + H+


a 2,3,4-saturated fatty acyl CoA + NADP+ = a trans-2-enoyl-CoA + NADPH + H+


an acyl-CoA + n (R)-methylmalonyl-CoA + 2n NADPH + 2n H+ = a multi-methyl-branched acyl-CoA + n CO2 + n coenzyme A + 2n NADP+
an acyl-CoA + glycine = an N-acylglycine + coenzyme A
a 1-lysophosphatidylcholine + 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 + NADP+ = a 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
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
a 2-oxo carboxylate + 2 an oxidized ferredoxin + coenzyme A = an acyl-CoA + CO2 + 2 a reduced ferredoxin + H+

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."

Yang10a: 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


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 Sat Nov 22, 2014, BIOCYC14A.