Record Information
Version2.0
Creation Date2012-05-31 13:48:58 -0600
Update Date2015-09-17 15:41:10 -0600
Secondary Accession Numbers
  • ECMDB01275
Identification
Name:Propionyl-CoA
Description:Propionyl-CoA is an intermediate in the metabolism of propanoate. Propionyl-CoA is a substrate for acetyl-CoA synthetase, propionyl-CoA synthetase and 2-methylcitrate synthase. It is also involved in beta-alanine metabolism, Valine, leucine abd isoleucine degradation and C5-branched dibasic acid metabolism pathways.
Structure
Thumb
Synonyms:
  • 2-methylacetyl-CoA
  • 2-methylacetyl-Coenzyme A
  • a-Methylacetyl-CoA
  • a-Methylacetyl-coenzyme A
  • Alpha-methylacetyl-CoA
  • Alpha-methylacetyl-Coenzyme A
  • N-Propionyl-CoA
  • Propanoyl-CoA
  • Propanoyl-Coenzyme A
  • Propionyl-CoA
  • Propionyl-coenzyme A
  • α-Methylacetyl-CoA
  • α-Methylacetyl-coenzyme A
Chemical Formula:C24H40N7O17P3S
Weight:Average: 823.597
Monoisotopic: 823.141423115
InChI Key:QAQREVBBADEHPA-UXYNFSPESA-N
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)/t13-,17-,18-,19?,23-/m1/s1
CAS number:317-66-8
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name:propionyl-coa
SMILES:CCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.27 mg/mLALOGPS
logP-0.31ALOGPS
logP-6.3ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity176.83 m3·mol-1ChemAxon
Polarizability73.8 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
2-Ketobutyric acid + Coenzyme A > Formic acid + Propionyl-CoA
Water + Oxalacetic acid + Propionyl-CoA <> Methylcitric acid + Coenzyme A + Hydrogen ion + (2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate
Phosphate + Propionyl-CoA > Coenzyme A + Propanoyl phosphate
Hydrogen ion + (S)-Methylmalonyl-CoA <> Carbon dioxide + Propionyl-CoA
Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA
Adenosine triphosphate + Coenzyme A + Propionic acid > ADP + Phosphate + Propionyl-CoA
Propionyl-CoA + Phosphate <> Propanoyl phosphate + Coenzyme A
(S)-Methylmalonyl-CoA <> Propionyl-CoA + Carbon dioxide
Propinol adenylate + Coenzyme A <> Adenosine monophosphate + Propionyl-CoA
Propionyl-CoA + Acetyl-CoA <> Coenzyme A + 2-Methylacetoacetyl-CoA
Methylcitric acid + Coenzyme A <> Propionyl-CoA + Oxalacetic acid + Water
Propionyl-CoA + Chenodeoxycholoyl-CoA <> Coenzyme A + 3alpha,7alpha-Dihydroxy-5beta-cholestanoyl-CoA
2-Ketobutyric acid + Coenzyme A <> Propionyl-CoA + Formic acid
Oxalacetic acid + Water + Propionyl-CoA <> Hydrogen ion + Methylcitric acid + Coenzyme A
Propionyl-CoA + Water + Glyoxylic acid <> 2-hydroxyglutarate + Hydrogen ion + Coenzyme A
2-Ketobutyric acid + Coenzyme A > Propionyl-CoA + Formic acid
Coenzyme A + Propionic acid + Adenosine triphosphate > Propionyl-CoA + Pyrophosphate + Adenosine monophosphate
Adenosine triphosphate + Hydrogen carbonate + Propionyl-CoA > Hydrogen ion + ADP + Phosphate + (S)-Methylmalonyl-CoA
Propionyl-CoA + Phosphate > Propanoyl phosphate + Coenzyme A
Propionyl-CoA + Succinic acid <> Propionic acid + Succinyl-CoA
Hydrogen ion + R-Methylmalonyl-CoA > Propionyl-CoA + Carbon dioxide
Propionyl-CoA + Water + Oxalacetic acid > (2R,3S)-2-Hydroxybutane-1,2,3-tricarboxylate + CoA
Adenosine triphosphate + Propionic acid + CoA > Adenosine monophosphate + Pyrophosphate + Propionyl-CoA
(S)-Methylmalonyl-CoA > Propionyl-CoA + Carbon dioxide
Propionyl-CoA + Succinic acid > Propionic acid + Succinyl-CoA

SMPDB Pathways:
Conversion of Succinate to PropanoatePW002058 Pw002058Pw002058 greyscalePw002058 simple
Propanoate metabolismPW000940 Pw000940Pw000940 greyscalePw000940 simple
beta-Alanine metabolismPW000896 Pw000896Pw000896 greyscalePw000896 simple
propanoyl CoA degradationPW002057 Pw002057Pw002057 greyscalePw002057 simple
KEGG Pathways:
  • C5-Branched dibasic acid metabolism ec00660
  • Glycerolipid metabolism ec00561
  • Glyoxylate and dicarboxylate metabolism ec00630
  • Metabolic pathways eco01100
  • Microbial metabolism in diverse environments ec01120
  • Propanoate metabolism ec00640
  • Reductive carboxylate cycle (CO2 fixation) ec00720
  • Valine, leucine and isoleucine degradation ec00280
  • beta-Alanine metabolism ec00410
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
5± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1901000220-8d8b91979e9c40176540View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0912000000-7c91e2c2f2f0d7b4a3adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2901000000-4311d5cc2b23055e1e3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-9830230550-4bec7e3f4052a0f39eefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0560-4910100000-d7281a44fcd4120a6bcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-19dd2ec65951d55b39f7View in MoNA
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Sokatch, John R.; Sanders, Lois E.; Marshall, Vincent P. Oxidation of methylmalonate semialdehyde to propionyl coenzyme A in Pseudomonas aeruginosa grown on valine. Journal of Biological Chemistry (1968), 243(10), 2500-6.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15539
HMDB IDHMDB01275
Pubchem Compound ID439164
Kegg IDC00100
ChemSpider ID388310
WikipediaPropionyl-CoA
BioCyc IDPROPIONYL-COA
EcoCyc IDPROPIONYL-COA

Enzymes

General function:
Involved in formate C-acetyltransferase activity
Specific function:
Acetyl-CoA + formate = CoA + pyruvate
Gene Name:
pflB
Uniprot ID:
P09373
Molecular weight:
85357
Reactions
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in phosphate acetyltransferase activity
Specific function:
Acetyl-CoA + phosphate = CoA + acetyl phosphate
Gene Name:
pta
Uniprot ID:
P0A9M8
Molecular weight:
77171
Reactions
Acetyl-CoA + phosphate = CoA + acetyl phosphate.
General function:
Involved in catalytic activity
Specific function:
Activation of pyruvate formate-lyase 1 under anaerobic conditions by generation of an organic free radical, using S- adenosylmethionine and reduced flavodoxin as cosubstrates to produce 5'-deoxy-adenosine
Gene Name:
pflA
Uniprot ID:
P0A9N4
Molecular weight:
28204
Reactions
S-adenosyl-L-methionine + dihydroflavodoxin + [formate C-acetyltransferase]-glycine = 5'-deoxyadenosine + L-methionine + flavodoxin semiquinone + [formate C-acetyltransferase]-glycin-2-yl radical.
General function:
Involved in acetyl-CoA C-acyltransferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadA
Uniprot ID:
P21151
Molecular weight:
40876
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
General function:
Involved in acetate-CoA ligase activity
Specific function:
Enables the cell to use acetate during aerobic growth to generate energy via the TCA cycle, and biosynthetic compounds via the glyoxylate shunt. Acetylates CheY, the response regulator involved in flagellar movement and chemotaxis
Gene Name:
acs
Uniprot ID:
P27550
Molecular weight:
72093
Reactions
ATP + acetate + CoA = AMP + diphosphate + acetyl-CoA.
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Catalyzes the synthesis of 2-methylcitrate from propionyl-CoA and oxaloacetate. Also catalyzes the condensation of oxaloacetate with acetyl-CoA but with a lower specificity
Gene Name:
prpC
Uniprot ID:
P31660
Molecular weight:
43102
Reactions
Propanoyl-CoA + H(2)O + oxaloacetate = (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA.
General function:
Involved in catalytic activity
Specific function:
Acetyl-CoA + formate = CoA + pyruvate
Gene Name:
pflD
Uniprot ID:
P32674
Molecular weight:
85959
Reactions
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in formate C-acetyltransferase activity
Specific function:
Specific function unknown
Gene Name:
tdcE
Uniprot ID:
P42632
Molecular weight:
85935
Reactions
Propionyl-CoA + formate = CoA + 2-oxobutanoate.
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in catalytic activity
Specific function:
(S)-methylmalonyl-CoA = propanoyl-CoA + CO(2)
Gene Name:
mmcD
Uniprot ID:
P52045
Molecular weight:
29172
Reactions
(S)-methylmalonyl-CoA = propanoyl-CoA + CO(2).
General function:
Involved in catalytic activity
Specific function:
Acetyl-CoA + formate = CoA + pyruvate
Gene Name:
ybiW
Uniprot ID:
P75793
Molecular weight:
90125
Reactions
Acetyl-CoA + formate = CoA + pyruvate.
General function:
Involved in transferase activity
Specific function:
Catalyzes the final step of fatty acid oxidation in which acetyl-CoA is released and the CoA ester of a fatty acid two carbons shorter is formed. Strongly involved in the anaerobic degradation of long and medium-chain fatty acids in the presence of nitrate and weakly involved in the aerobic degradation of long- chain fatty acids
Gene Name:
fadI
Uniprot ID:
P76503
Molecular weight:
46530
Reactions
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the synthesis of propionyl-CoA from propionate and CoA. Also converts acetate to acetyl-CoA but with a lower specific activity
Gene Name:
prpE
Uniprot ID:
P77495
Molecular weight:
69350
Reactions
ATP + propanoate + CoA = AMP + diphosphate + propanoyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Specific function unknown
Gene Name:
ygfH
Uniprot ID:
P52043
Molecular weight:
53824
Reactions
Propanoyl-CoA + succinate = propionate + succinyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Acts as a radical domain for damaged PFL and possibly other radical proteins
Gene Name:
grcA
Uniprot ID:
P68066
Molecular weight:
14284