Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
Updated BioCyc iOS App now
available in iTunes store
twitter

MetaCyc Compound: propanoyl-CoA

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

Superclasses: an estera thioestera coenzyme A-activated compoundan acyl-CoAa 2,3,4-saturated fatty acyl CoAa short-chain 2,3,4-saturated fatty acyl CoA
an estera thioestera coenzyme A-activated compoundan acyl-CoAa short-chain acyl-CoAa 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): -484.70157Inferred 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+ → an (11Z)-enoyl-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) :
17-hydroxy-3-oxo-4-pregnane-20-carboxyl-CoA → androst-4-ene-3,17-dione + propanoyl-CoA
3-oxochol-4-en-24-oyl-CoA + propanoyl-CoA ← 3,24-dioxocholest-4-en-26-oyl-CoA + coenzyme A

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

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 :
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
3-oxochol-4-en-24-oyl-CoA + propanoyl-CoA ← 3,24-dioxocholest-4-en-26-oyl-CoA + coenzyme A

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 [iron-sulfur] cluster + coenzyme A → propanoyl-CoA + 2 a reduced ferredoxin [iron-sulfur] cluster + 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 + 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

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: acryloyl-CoA reductase, L-amino acid N-acyltransferase, butyryl-CoA:acetoacetate CoA-transferase, phosphotransbutyrylase, reduced holothin acetyltranferase, 2-amino-3-ketobutyrate CoA ligase, phosphotransacetylase, malyl coenzyme A lyase, glucosamine-1-phosphate acetyltransferase, acetyl-CoA:13-[O(2')-β-D-glucopyranosyl-β-D-glucopyranosyloxy]docosanoate acetyltransferase, mycothiol synthase, 27-O-demethyl-25-O-desacetyl-rifamycin SV O-acetyltransferase, β-ketoacyl-ACP synthase, homocitrate synthase, 6-methylsalicylate synthase, holothin acetyltranferase, 4-hydroxybutyrate CoA-transferase, phosphate acetyltransferase


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


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 Pathway Tools version 19.5 (software by SRI International) on Sun Feb 7, 2016, biocyc14.