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Record Information
Version1.0
Creation Date2016-09-30 22:43:29 UTC
Update Date2020-05-21 16:29:03 UTC
BMDB IDBMDB0001275
Secondary Accession Numbers
  • BMDB01275
Metabolite Identification
Common NamePropionyl-CoA
DescriptionPropionyl-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
Thumb
Synonyms
ValueSource
2-Methylacetyl-CoAHMDB
2-Methylacetyl-coenzyme AHMDB
alpha-Methylacetyl-CoAHMDB
alpha-Methylacetyl-coenzyme AHMDB
Propanoyl-CoAHMDB
Propanoyl-coenzyme AHMDB
Propionyl-coenzyme AHMDB
Chemical FormulaC24H40N7O17P3S
Average Molecular Weight823.597
Monoisotopic Molecular Weight823.141423115
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({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 Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(propanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry Number317-66-8
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
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 KeyQAQREVBBADEHPA-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.
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 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count21ChemAxon
Refractivity176.83 m³·mol⁻¹ChemAxon
Polarizability72.51 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1921000110-a902ba2e846c5fa3a6f6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-1911000000-73f7c171e662ee7ccd1dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-1910000000-e82bdc99f5bada8c440eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a7i-9830232560-d45384d1d1a3fe0dd614View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-4910200000-2a67602fe8e4a74a6abeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-8900100000-d3e8a1b9393d73c218b4View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Mitochondria
  • Peroxisome
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001275
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022529
KNApSAcK IDNot Available
Chemspider ID388310
KEGG Compound IDC00100
BioCyc IDNot Available
BiGG ID33852
Wikipedia LinkPropionyl-CoA
METLIN ID6130
PubChem Compound439164
PDB IDNot Available
ChEBI ID15539
References
Synthesis ReferenceSokatch, 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 ReferencesNot 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 phosphatedetails
Propionyl-CoA + Hydrogen carbonate + Adenosine triphosphate → S-Methylmalonyl-CoA + ADP + Hydrogendetails
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 carbonatedetails
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 + Pyrophosphatedetails
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-CoAdetails
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 phosphatedetails
Propionyl-CoA + Hydrogen carbonate + Adenosine triphosphate → S-Methylmalonyl-CoA + ADP + Hydrogendetails
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 + NADHdetails
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 + NADHdetails
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 + NADHdetails
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 flavoproteindetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
DLD
Uniprot ID:
F1N206
Molecular weight:
54187.0
Reactions
2-Ketobutyric acid + Coenzyme A + NAD → Propionyl-CoA + NADHdetails
General function:
Not Available
Specific function:
Not Available
Gene Name:
AceCS2
Uniprot ID:
Q9BEA3
Molecular weight:
74310.0
Reactions
Propionyl-CoA + Adenosine monophosphate + Pyrophosphate → Propinol adenylate + Adenosine triphosphate + Pantetheinedetails