Propionyl-CoA (ECMDB01275) (M2MDB000321)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 13:48:58 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-09-17 15:41:10 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | 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. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Fatty Acyls | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Fatty acyl thioesters | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Acyl CoAs | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -4 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | 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 + 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 + Formic acid > CoA + 2-Ketobutyric acid Propionyl-CoA + NADP <> Acrylyl-CoA + NADPH + Hydrogen ion Adenosine triphosphate + Propionic acid + Coenzyme A <> Adenosine monophosphate + Pyrophosphate + Propionyl-CoA 2-Ketobutyric acid + Coenzyme A > Formic acid + Propionyl-CoA + Propionyl-CoA More...Propionyl-CoA + Phosphate + Propionyl-CoA > Coenzyme A + propanoyl phosphate + Propanoyl phosphate Propionic acid + Adenosine triphosphate + Coenzyme A > Propionyl-CoA + Adenosine monophosphate + Pyrophosphate + Propionyl-CoA Propionyl-CoA + Water + Oxalacetic acid + Propionyl-CoA > Coenzyme A + Hydrogen ion + 2-Methylcitric acid + Methylcitric acid Succinic acid + Propionyl-CoA + Propionyl-CoA > Propionic acid + Succinyl-CoA + Succinyl-CoA Methylmalonyl-CoA + Hydrogen ion > Carbon dioxide + Propionyl-CoA + Propionyl-CoA R-Methylmalonyl-CoA + Hydrogen ion > Propionyl-CoA + Carbon dioxide 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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: |
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EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Find out more about how we convert literature concentrations. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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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