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Showing metabocard for Propionyl-CoA (BMDB0001275)
Record Information | |||||||||||||||||
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Version | 1.0 | ||||||||||||||||
Creation Date | 2016-09-30 22:43:29 UTC | ||||||||||||||||
Update Date | 2020-05-21 16:29:03 UTC | ||||||||||||||||
BMDB ID | BMDB0001275 | ||||||||||||||||
Secondary Accession Numbers |
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Metabolite Identification | |||||||||||||||||
Common Name | Propionyl-CoA | ||||||||||||||||
Description | Propionyl-CoA, also known as propionyl-coa, 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. Propionyl-CoA is possibly soluble (in water) and a strong basic compound (based on its pKa). Propionyl-CoA participates in a number of enzymatic reactions, within cattle. In particular, Propionyl-CoA and L-carnitine can be converted into propionylcarnitine through the action of the enzyme carnitine O-acetyltransferase. In addition, Propionyl-CoA and L-carnitine can be converted into propionylcarnitine through the action of the enzyme carnitine O-acetyltransferase. In cattle, propionyl-CoA is involved in the metabolic pathway called the oxidation OF branched-chain fatty acids pathway. Propionyl-CoA is a potentially toxic compound. | ||||||||||||||||
Structure | |||||||||||||||||
Synonyms |
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Chemical Formula | C24H40N7O17P3S | ||||||||||||||||
Average Molecular Weight | 823.597 | ||||||||||||||||
Monoisotopic Molecular Weight | 823.141423115 | ||||||||||||||||
IUPAC Name | Not Available | ||||||||||||||||
Traditional Name | Not Available | ||||||||||||||||
CAS Registry Number | 317-66-8 | ||||||||||||||||
SMILES | Not Available | ||||||||||||||||
InChI Identifier | 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 | ||||||||||||||||
InChI Key | QAQREVBBADEHPA-UXYNFSPESA-N | ||||||||||||||||
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 | Not Available | ||||||||||||||||
Ontology | |||||||||||||||||
Status | Expected but not Quantified | ||||||||||||||||
Origin |
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Biofunction | Not Available | ||||||||||||||||
Application | Not Available | ||||||||||||||||
Cellular locations |
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Physical Properties | |||||||||||||||||
State | Solid | ||||||||||||||||
Experimental Properties |
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Predicted Properties | Not Available | ||||||||||||||||
Spectra | |||||||||||||||||
Spectra |
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Biological Properties | |||||||||||||||||
Cellular Locations |
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Biospecimen Locations | Not Available | ||||||||||||||||
Pathways | |||||||||||||||||
Normal Concentrations | |||||||||||||||||
Not Available | |||||||||||||||||
Abnormal Concentrations | |||||||||||||||||
Not Available | |||||||||||||||||
External Links | |||||||||||||||||
HMDB ID | HMDB0001275 | ||||||||||||||||
DrugBank ID | Not Available | ||||||||||||||||
Phenol Explorer Compound ID | Not Available | ||||||||||||||||
FooDB ID | FDB022529 | ||||||||||||||||
KNApSAcK ID | Not Available | ||||||||||||||||
Chemspider ID | 388310 | ||||||||||||||||
KEGG Compound ID | C00100 | ||||||||||||||||
BioCyc ID | Not Available | ||||||||||||||||
BiGG ID | 33852 | ||||||||||||||||
Wikipedia Link | Propionyl-CoA | ||||||||||||||||
METLIN ID | 6130 | ||||||||||||||||
PubChem Compound | 439164 | ||||||||||||||||
PDB ID | Not Available | ||||||||||||||||
ChEBI ID | 15539 | ||||||||||||||||
References | |||||||||||||||||
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 | ||||||||||||||||
General References | Not Available |
Enzymes
- General function:
- Involved in ATP binding
- Specific function:
- This is one of the 2 subunits of the biotin-dependent propionyl-CoA carboxylase (PCC), a mitochondrial enzyme involved in the catabolism of odd chain fatty acids, branched-chain amino acids isoleucine, threonine, methionine, and valine and other metabolites. Propionyl-CoA carboxylase catalyzes the carboxylation of propionyl-CoA/propanoyl-CoA to D-methylmalonyl-CoA/(S)-methylmalonyl-CoA (By similarity). Within the holoenzyme, the alpha subunit catalyzes the ATP-dependent carboxylation of the biotin carried by the biotin carboxyl carrier (BCC) domain, while the beta subunit then transfers the carboxyl group from carboxylated biotin to propionyl-CoA (By similarity). Propionyl-CoA carboxylase also significantly acts on butyryl-CoA/butanoyl-CoA, which is converted to ethylmalonyl-CoA/(2S)-ethylmalonyl-CoA (By similarity). Other alternative minor substrates include (2E)-butenoyl-CoA/crotonoyl-CoA (By similarity).
- Gene Name:
- PCCB
- Uniprot ID:
- Q2TBR0
- Molecular weight:
- 58311.0
Reactions
Propionyl-CoA + Adenosine triphosphate + Hydrogen carbonate → S-Methylmalonyl-CoA + ADP + Hydrogen phosphate | details |
Propionyl-CoA + Hydrogen carbonate + Adenosine triphosphate → S-Methylmalonyl-CoA + ADP + Hydrogen | details |
- General function:
- Energy production and conversion
- Specific function:
- Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
- Gene Name:
- ALDH6A1
- Uniprot ID:
- Q07536
- Molecular weight:
- 58063.0
Reactions
(S)-Methylmalonic acid semialdehyde + Water + NAD + Coenzyme A → Propionyl-CoA + NADH + Hydrogen carbonate | details |
- General function:
- Lipid transport and metabolism
- Specific function:
- Catalyzes the synthesis of acetyl-CoA from short-chain fatty acids (By similarity). Propionate is the preferred substrate but can also utilize acetate and butyrate with a much lower affinity.
- Gene Name:
- ACSS3
- Uniprot ID:
- A7MB45
- Molecular weight:
- 74805.0
Reactions
Propinol adenylate + Adenosine triphosphate + Pantetheine → Propionyl-CoA + Adenosine monophosphate + Pyrophosphate | details |
- General function:
- Lipid transport and metabolism
- Specific function:
- In the production of energy from fats, this is one of the enzymes that catalyzes the last step of the mitochondrial beta-oxidation pathway, an aerobic process breaking down fatty acids into acetyl-CoA. Using free coenzyme A/CoA, catalyzes the thiolytic cleavage of medium- to long-chain unbranched 3-oxoacyl-CoAs into acetyl-CoA and a fatty acyl-CoA shortened by two carbon atoms. Also catalyzes the condensation of two acetyl-CoA molecules into acetoacetyl-CoA and could be involved in the production of ketone bodies. Also displays hydrolase activity on various fatty acyl-CoAs (By similarity). Thereby, could be responsible for the production of acetate in a side reaction to beta-oxidation (By similarity). Abolishes BNIP3-mediated apoptosis and mitochondrial damage (By similarity).
- Gene Name:
- ACAA2
- Uniprot ID:
- Q3T0R7
- Molecular weight:
- 42131.0
Reactions
2-Methylacetoacetyl-CoA + Coenzyme A → Propionyl-CoA + Acetyl-CoA | details |
- General function:
- Lipid transport and metabolism
- Specific function:
- Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
- Gene Name:
- SCP2
- Uniprot ID:
- P07857
- Molecular weight:
- 58577.0
- General function:
- Involved in ATP binding
- Specific function:
- Pyruvate carboxylase catalyzes a 2-step reaction, involving the ATP-dependent carboxylation of the covalently attached biotin in the first step and the transfer of the carboxyl group to pyruvate in the second. Catalyzes in a tissue specific manner, the initial reactions of glucose (liver, kidney) and lipid (adipose tissue, liver, brain) synthesis from pyruvate (By similarity).
- Gene Name:
- PC
- Uniprot ID:
- Q29RK2
- Molecular weight:
- 129698.0
Reactions
Propionyl-CoA + Adenosine triphosphate + Hydrogen carbonate → S-Methylmalonyl-CoA + ADP + Hydrogen phosphate | details |
Propionyl-CoA + Hydrogen carbonate + Adenosine triphosphate → S-Methylmalonyl-CoA + ADP + Hydrogen | details |
- General function:
- Energy production and conversion
- Specific function:
- The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
- Gene Name:
- BCKDHA
- Uniprot ID:
- P11178
- Molecular weight:
- 51678.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADH | details |
- General function:
- Energy production and conversion
- Specific function:
- The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
- Gene Name:
- BCKDHB
- Uniprot ID:
- P21839
- Molecular weight:
- 42935.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADH | details |
- General function:
- Energy production and conversion
- Specific function:
- The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3). Within this complex, the catalytic function of this enzyme is to accept, and to transfer to coenzyme A, acyl groups that are generated by the branched-chain alpha-keto acid decarboxylase component.
- Gene Name:
- DBT
- Uniprot ID:
- P11181
- Molecular weight:
- 53410.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADH | details |
- General function:
- Lipid transport and metabolism
- Specific function:
- Acyl-CoA dehydrogenase specific for acyl chain lengths of 4 to 16 that catalyzes the initial step of fatty acid beta-oxidation. Utilizes the electron transfer flavoprotein (ETF) as an electron acceptor to transfer electrons to the main mitochondrial respiratory chain via ETF-ubiquinone oxidoreductase (ETF dehydrogenase).
- Gene Name:
- ACADM
- Uniprot ID:
- Q3SZB4
- Molecular weight:
- 46573.0
Reactions
Acrylyl-CoA + electron-transfer flavoprotein → Propionyl-CoA + Reduced electron-transfer flavoprotein | details |