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MetaCyc Compound: propanoyl-CoA

Synonyms: n-propionyl-CoA, propionyl-CoA, propionyl-coenzyme A

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

Chemical Formula: C24H36N7O17P3S

Molecular Weight: 819.57 Daltons

Monoisotopic Molecular Weight: 823.1414231161 Daltons

propanoyl-CoA compound structure

SMILES: CCC(=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/C24H40N7O17P3S/c1-4-15(33)52-8-7-26-14(32)5-6-27-22(36)19(35)24(2,3)10-45-51(42,43)48-50(40,41)44-9-13-18(47-49(37,38)39)17(34)23(46-13)31-12-30-16-20(25)28-11-29-21(16)31/h11-13,17-19,23,34-35H,4-10H2,1-3H3,(H,26,32)(H,27,36)(H,40,41)(H,42,43)(H2,25,28,29)(H2,37,38,39)/p-4/t13-,17-,18-,19+,23-/m1/s1

InChIKey: InChIKey=QAQREVBBADEHPA-IEXPHMLFSA-J

Unification Links: CAS:317-66-8 , ChEBI:57392 , HMDB:HMDB01275 , IAF1260:33852 , KEGG:C00100 , MetaboLights:MTBLC57392 , PubChem:45266613

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -484.70157 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

2-oxobutanoate degradation II :
propanoyl-CoA + H2O → propanoate + coenzyme A + H+

aclacinomycin biosynthesis , daunorubicin biosynthesis :
propanoyl-CoA + 9 malonyl-CoA + polyketide synthase + 9 H+ → 3,5,7,9,11,13,15,17,19-nonaoxohenicosanoyl-[acp] + 9 CO2 + 10 coenzyme A

β-alanine biosynthesis II :
propanoyl-CoA + an oxidized electron-transfer flavoprotein + H+ → acryloyl-CoA + a reduced electron-transfer flavoprotein

erythromycin D biosynthesis :
propanoyl-CoA + 6 (S)-methylmalonyl-CoA + 6 NADPH + 12 H+ → 6-deoxyerythronolide B + 6 CO2 + 7 coenzyme A + 6 NADP+ + H2O

propanoyl-CoA degradation II :
propanoyl-CoA + oxygen → acryloyl-CoA + hydrogen peroxide

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

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

Not in pathways:
a short-chain acyl-CoA + H2O → a short-chain carboxylate + coenzyme A + H+

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

Not in pathways:
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an acyl-CoA + 2 a ferrocytochrome b5 + oxygen + 2 H+ → a cis Δ11 acyl-CoA + 2 a ferricytochrome b5 + 2 H2O

Reactions known to produce the compound:

2,4-dinitrotoluene degradation :
methylmalonate semialdehyde + coenzyme A + NAD+ + H2O → propanoyl-CoA + hydrogen carbonate + NADH + H+

2-methylcitrate cycle I , 2-methylcitrate cycle II , β-alanine biosynthesis II , L-isoleucine biosynthesis IV :
propanoate + ATP + coenzyme A → propanoyl-CoA + AMP + diphosphate

2-oxobutanoate degradation I , L-threonine degradation V :
2-oxobutanoate + coenzyme A + NAD+propanoyl-CoA + CO2 + NADH

3,3'-dithiodipropanoate degradation , 3,3'-thiodipropanoate degradation :
3-sulfinopropanoyl-CoA + H2O → propanoyl-CoA + sulfite + H+

3-hydroxypropanoate cycle , 3-hydroxypropanoate/4-hydroxybutanate cycle , glyoxylate assimilation :
propanoyl-CoA + NADP+ ← acryloyl-CoA + NADPH + H+

bile acid biosynthesis, neutral pathway :
3α,7α-dihydroxy-24-oxo-5β-cholestanoyl CoA + coenzyme A → chenodeoxycholoyl-CoA + propanoyl-CoA
3α,7α,12α-trihydroxy-24-oxo-5-β-cholestanoyl CoA + coenzyme A → choloyl-CoA + propanoyl-CoA

cholesterol degradation to androstenedione I (cholesterol oxidase) :
3,24-dioxocholest-4-en-26-oyl-CoA + coenzyme A → 3-oxochol-4-en-24-oyl-CoA + propanoyl-CoA
17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA → androst-4-ene-3,17-dione + propanoyl-CoA

cholesterol degradation to androstenedione II (cholesterol dehydrogenase) :
3,24-dioxocholest-4-en-26-oyl-CoA + coenzyme A → 3-oxochol-4-en-24-oyl-CoA + propanoyl-CoA
17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA → androst-4-ene-3,17-dione + propanoyl-CoA

conversion of succinate to propanoate :
(R)-methylmalonyl-CoA + H+propanoyl-CoA + CO2

L-threonine degradation I :
2-oxobutanoate + coenzyme A → propanoyl-CoA + formate

L-valine degradation I :
(S)-methylmalonate-semialdehyde + coenzyme A + NAD+ + H2O → propanoyl-CoA + hydrogen carbonate + NADH + H+

pyruvate fermentation to propanoate II (acrylate pathway) :
propanoyl-CoA + NAD+ ← acryloyl-CoA + NADH + H+

sitosterol degradation to androstenedione :
3,24-dioxocholest-4-en-26-oyl-CoA + coenzyme A → 3-oxochol-4-en-24-oyl-CoA + propanoyl-CoA
17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA → androst-4-ene-3,17-dione + propanoyl-CoA
3-oxo-24-(isopropanoyl)-cholest-4,24-dien-26-oyl-CoA + H2O → 3,24-dioxo-cholest-4-en-26-oate + propanoyl-CoA

Not in pathways:
3-hydroxypropanoate + ATP + coenzyme A + NADPH + H+propanoyl-CoA + AMP + NADP+ + diphosphate + H2O

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

Reactions known to both consume and produce the compound:

2-methylbutanoate biosynthesis :
2-methylacetoacetyl-CoA + coenzyme A ↔ propanoyl-CoA + acetyl-CoA
acetyl-CoA + propanoate ↔ acetate + propanoyl-CoA

2-methylcitrate cycle I , 2-methylcitrate cycle II :
propanoyl-CoA + oxaloacetate + H2O ↔ (2S,3S)-2-methylcitrate + coenzyme A + H+

2-oxobutanoate degradation II , L-isoleucine biosynthesis IV :
2-oxobutanoate + 2 an oxidized ferredoxin + coenzyme A ↔ propanoyl-CoA + 2 a reduced ferredoxin + CO2 + H+

3-hydroxypropanoate cycle , 3-hydroxypropanoate/4-hydroxybutanate cycle , propanoyl CoA degradation I :
propanoyl-CoA + ATP + hydrogen carbonate ↔ (S)-methylmalonyl-CoA + ADP + phosphate + H+

anaerobic energy metabolism (invertebrates, mitochondrial) :
propanoyl-CoA + ATP + hydrogen carbonate ↔ (S)-methylmalonyl-CoA + ADP + phosphate + H+
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

androstenedione degradation :
propanal + coenzyme A + NAD+propanoyl-CoA + NADH + H+

conversion of succinate to propanoate :
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

ethylmalonyl-CoA pathway , glyoxylate assimilation :
(2R,3S)-β-methylmalyl-CoA ↔ glyoxylate + propanoyl-CoA

L-1,2-propanediol degradation :
propanal + coenzyme A + NAD+propanoyl-CoA + NADH + H+
propanoyl-CoA + phosphate ↔ propanoyl phosphate + coenzyme A

L-isoleucine degradation I :
2-methylacetoacetyl-CoA + coenzyme A ↔ propanoyl-CoA + acetyl-CoA

L-threonine degradation I :
propanoyl-CoA + phosphate ↔ propanoyl phosphate + coenzyme A

methylaspartate cycle :
(2R,3S)-β-methylmalyl-CoA ↔ glyoxylate + propanoyl-CoA
propanoyl-CoA + ATP + hydrogen carbonate ↔ (S)-methylmalonyl-CoA + ADP + phosphate + H+

pyruvate fermentation to propanoate I :
pyruvate + (S)-methylmalonyl-CoA ↔ oxaloacetate + propanoyl-CoA
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

pyruvate fermentation to propanoate II (acrylate pathway) :
acetyl-CoA + propanoate ↔ acetate + propanoyl-CoA
propanoyl-CoA + (R)-lactate ↔ propanoate + (R)-lactoyl-CoA

Not in pathways:
propanoate + ATP + coenzyme A ↔ propanoyl-CoA + ADP + phosphate

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:
(S)-methylmalonyl-CoA + H+ = CO2 + propanoyl-CoA
propanoyl-CoA + 4,8,12-trimethyltridecanoyl-CoA = 3-oxopristanoyl-CoA + coenzyme A
acetyl-CoA + propanoyl-CoA = β-ketovaleryl-CoA + coenzyme A
propanoyl-CoA + glyoxylate + H2O = 2-hydroxyglutarate + coenzyme A + H+
(S)-lactate + propanoyl-CoA = propanoate + (S)-lactoyl-CoA

Not in pathways:
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 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+ = a trans Δ11 acyl-CoA + 2 a ferricytochrome b5 + 2 H2O
a 2-oxo carboxylate + 2 an oxidized ferredoxin + coenzyme A = an acyl-CoA + CO2 + 2 a reduced ferredoxin + H+

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

Inhibitor (Competitive) of: tiglyl-CoA hydrase [Roberts78]

Inhibitor (Mechanism unknown) of: citrate synthase [Man95] , DL-methylmalonyl-CoA racemase [Stabler85]

This compound has been characterized as an alternative substrate of the following enzymes: β-ketoacyl-ACP synthase , malyl coenzyme A lyase , acetyl-CoA:13-[O(2')-β-D-glucopyranosyl-β-D-glucopyranosyloxy]docosanoate acetyltransferase , 6-methylsalicylate synthase , 27-O-demethyl-25-O-desacetyl-rifamycin SV O-acetyltransferase , phosphotransbutyrylase , mycothiol synthase , acryloyl-CoA reductase , phosphotransacetylase , 2-amino-3-ketobutyrate CoA ligase , glucosamine-1-phosphate acetyltransferase , L-amino acid N-acyltransferase , butyryl-CoA:acetoacetate CoA-transferase , phosphate acetyltransferase , holothin acetyltranferase , 4-hydroxybutyrate CoA-transferase


References

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

Man95: Man WJ, Li Y, O'Connor CD, Wilton DC (1995). "The binding of propionyl-CoA and carboxymethyl-CoA to Escherichia coli citrate synthase." Biochim Biophys Acta 1250(1);69-75. PMID: 7612655

Roberts78: Roberts CM, Conrad RS, Sokatch JR (1978). "The role of enoyl-coa hydratase in the metabolism of isoleucine by Pseudomonas putida." Arch Microbiol 117(1);99-108. PMID: 678016

Stabler85: Stabler SP, Marcell PD, Allen RH (1985). "Isolation and characterization of DL-methylmalonyl-coenzyme A racemase from rat liver." Arch Biochem Biophys 241(1);252-64. PMID: 2862845


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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 Sat Sep 5, 2015, BIOCYC14B.