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
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

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

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:25245439

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 + a polyketide synthase containing an [acp] domain + 10 H+ → 3,5,7,9,11,13,15,17,19-nonaoxohenicosanoyl-[acp] + 9 CO2 + 10 coenzyme A

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

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


a short-chain acyl-CoA + H2O → a short-chain carboxylate + coenzyme A + H+

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


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:

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

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

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

3,3'-dithiodipropionate degradation , 3,3'-thiodipropionate 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+

β-alanine biosynthesis II :
propanoate + ATP + coenzyme A → propanoyl-CoA + AMP + diphosphate
propanoyl-CoA + an oxidized electron-transfer flavoprotein ← acryloyl-CoA + a reduced electron-transfer flavoprotein

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
3-oxo-23,24-bisnorchol-4-en-17-ol-22-oyl-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
3-oxo-23,24-bisnorchol-4-en-17-ol-22-oyl-CoA → androst-4-ene-3,17-dione + propanoyl-CoA

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

pyruvate fermentation to propionate 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
3-oxo-23,24-bisnorchol-4-en-17-ol-22-oyl-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

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

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

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

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


a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to both consume and produce the compound:

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

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

2-oxobutanoate degradation II , 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 , propionyl CoA degradation :
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 propionate :
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

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

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

L-1,2-propanediol degradation :
propanal + coenzyme A + NAD+propanoyl-CoA + NADH + H+
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 propionate I :
pyruvate + (S)-methylmalonyl-CoA ↔ oxaloacetate + propanoyl-CoA
propanoyl-CoA + succinate ↔ propanoate + succinyl-CoA

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

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

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


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:
(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


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+

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]


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 SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, biocyc13.