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MetaCyc Compound: icosanoyl-CoA

Synonyms: eicosanoyl-CoA, arachidoyl-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:
This is the acyl-CoA form of arachidate.

Citations: [King07]

Chemical Formula: C41H70N7O17P3S

Molecular Weight: 1058.0 Daltons

Monoisotopic Molecular Weight: 1061.4074742075002 Daltons

icosanoyl-CoA compound structure

SMILES: CCCCCCCCCCCCCCCCCCCC(=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/C41H74N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-32(50)69-25-24-43-31(49)22-23-44-39(53)36(52)41(2,3)27-62-68(59,60)65-67(57,58)61-26-30-35(64-66(54,55)56)34(51)40(63-30)48-29-47-33-37(42)45-28-46-38(33)48/h28-30,34-36,40,51-52H,4-27H2,1-3H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/p-4/t30-,34-,35-,36+,40-/m1/s1

InChIKey: InChIKey=JYLSVNBJLYCSSW-IBYUJNRCSA-J

Unification Links: ChEBI:57380, HMDB:HMDB04258, KEGG:C02041, PubChem:25203411

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): -107.94346Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(5Z)-icosenoate biosynthesis :
icosanoyl-CoA + 2 a ferrocytochrome b5 + oxygen + 2 H+ → (5Z)-icosenoyl-CoA + 2 a ferricytochrome b5 + 2 H2O

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

Not in pathways:
icosanoyl-CoA + H2O → arachidate + coenzyme A + H+

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

Reactions known to produce the compound:

very long chain fatty acid biosynthesis II :
icosanoyl-CoA + NADP+trans-arachido-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:
an arachidoyl-[acp] + coenzyme A = icosanoyl-CoA + a holo-[acyl-carrier protein]
icosanoyl-CoA + 4 (R)-methylmalonyl-CoA + 8 NADPH + 12 H+ = C32 mycocerosyl-CoA + 4 CO2 + 4 coenzyme A + 8 NADP+ + 4 H2O
icosanoyl-CoA + 3 (R)-methylmalonyl-CoA + 6 NADPH + 9 H+ = C29 mycocerosyl-CoA + 3 CO2 + 3 coenzyme A + 6 NADP+ + 3 H2O
icosanoyl-CoA + a malonyl-[acp] + H+ = a 3-oxo-behenoyl-[acp] + CO2 + coenzyme A
icosanoyl-CoA + 1-dodecanol = arachidoyl dodecanoate + 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

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 icosanoyl-CoA, sorted by the type of inhibition, are:

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

Credits:
Created 26-Mar-2012 by Caspi R, SRI International


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.

King07: King A, Nam JW, Han J, Hilliard J, Jaworski JG (2007). "Cuticular wax biosynthesis in petunia petals: cloning and characterization of an alcohol-acyltransferase that synthesizes wax-esters." Planta 226(2);381-94. PMID: 17323080

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
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