ContaminantDB: Propionyl-CoA

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (28)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:20 UTC

Update Date

2026-08-22 04:12:48 UTC

Accession Number

CHEM003407

Identification

Common Name

Propionyl-CoA

Class

Small Molecule

Description

Propionyl-CoA is an endogenous biological metabolite with the formula C24H40N7O17P3S. Propionyl-CoA belongs to the fatty acyl thioesters, a subclass of fatty acyls within the organic compounds. With an average molecular weight of 823.60 g/mol, Propionyl-CoA is a heavy molecule. It exists as a solid at room temperature. Propionyl-CoA is an intermediate in the metabolism of propanoate and serves as a substrate for several enzymes, including Propionyl-CoA carboxylase alpha and beta chains, Acetyl-coenzyme A synthetase, and various Acyl-CoA dehydrogenases. Its recorded protein target is the Propionyl-CoA carboxylase complex B subunit (pccB). In propionic aciduria, caused by propionyl coenzyme A carboxylase deficiency, Propionyl-CoA accumulates in the mitochondria.

Contaminant Sources

FooDB Chemicals
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Ester
Ether
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Methylacetyl-CoA	HMDB
2-Methylacetyl-coenzyme A	HMDB
alpha-Methylacetyl-CoA	HMDB
alpha-Methylacetyl-coenzyme A	HMDB
Propanoyl-CoA	HMDB
Propanoyl-coenzyme A	HMDB
Propionyl-coenzyme A	HMDB

Chemical Formula

C₂₄H₄₀N₇O₁₇P₃S

Average Molecular Mass

823.597 g/mol

Monoisotopic Mass

823.141 g/mol

CAS Registry 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 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]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

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 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

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane
Mitochondria
Peroxisome

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Oxidation of Branched Chain Fatty Acids	SMP00030	Not Available
Phytanic Acid Peroxisomal Oxidation	SMP00450	Not Available
Propanoate Metabolism	SMP00016	map00640
Threonine and 2-Oxobutanoate Degradation	SMP00452	Not Available
Valine, Leucine and Isoleucine Degradation	SMP00032	map00280
Propionic Acidemia	SMP00236	Not Available
Phytanic Acid Peroxisomal Oxidation	SMP0000450	Not Available
Valine, Leucine, and Isoleucine Degradation	SMP0000032	Not Available
beta-Ketothiolase Deficiency	SMP0000173	Not Available
2-Methyl-3-hydroxybutyryl-CoA Dehydrogenase Deficiency	SMP0000137	Not Available
Propionic Acidemia	SMP0000236	Not Available
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency	SMP0000138	Not Available
Maple Syrup Urine Disease	SMP0000199	Not Available
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I	SMP0000237	Not Available
3-Methylglutaconic Aciduria Type I	SMP0000139	Not Available
3-Methylglutaconic Aciduria Type III	SMP0000140	Not Available
Methylmalonate Semialdehyde Dehydrogenase Deficiency	SMP0000384	Not Available
Methylmalonic Aciduria	SMP0000200	Not Available
Isovaleric Aciduria	SMP0000238	Not Available
Refsum Disease	SMP0000451	Not Available
Bile Acid Biosynthesis	SMP0000035	Not Available
Propanoate Metabolism	SMP0000016	Not Available
Oxidation of Branched-Chain Fatty Acids	SMP0000030	Not Available
Threonine and 2-Oxobutanoate Degradation	SMP0000452	Not Available
Congenital Bile Acid Synthesis Defect Type II	SMP0000314	Not Available
Congenital Bile Acid Synthesis Defect Type III	SMP0000318	Not Available
Zellweger Syndrome	SMP0000316	Not Available
Cerebrotendinous Xanthomatosis (CTX)	SMP0000315	Not Available
Malonic Aciduria	SMP0000198	Not Available
Methylmalonic Aciduria Due to Cobalamin-Related Disorders	SMP0000201	Not Available
3-Methylglutaconic Aciduria Type IV	SMP0000141	Not Available
Malonyl-CoA Decarboxylase Deficiency	SMP0000502	Not Available
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency	SMP0000521	Not Available
3-Hydroxyisobutyric Aciduria	SMP0000522	Not Available
Isobutyryl-CoA Dehydrogenase Deficiency	SMP0000523	Not Available
Isovaleric Acidemia	SMP0000524	Not Available
Valproic Acid Metabolism Pathway	SMP0000635	Not Available
27-Hydroxylase Deficiency	SMP0000720	Not Available
Malonic Aciduria	SMP0125619	Not Available
Methylmalonic Aciduria Due to Cobalamin-Related Disorders	SMP0125620	Not Available
Malonyl-CoA Decarboxylase Deficiency	SMP0125621	Not Available
beta-Ketothiolase Deficiency	SMP0125657	Not Available
2-Methyl-3-hydroxybutyryl-CoA Dehydrogenase Deficiency	SMP0125658	Not Available
Propionic Acidemia	SMP0125659	Not Available
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency	SMP0125660	Not Available
Maple Syrup Urine Disease	SMP0125661	Not Available
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I	SMP0125662	Not Available
3-Methylglutaconic Aciduria Type I	SMP0125664	Not Available
3-Methylglutaconic Aciduria Type III	SMP0125667	Not Available
Methylmalonate Semialdehyde Dehydrogenase Deficiency	SMP0125669	Not Available
Methylmalonic Aciduria	SMP0125670	Not Available
Isovaleric Aciduria	SMP0125671	Not Available
3-Methylglutaconic Aciduria Type IV	SMP0125672	Not Available
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency	SMP0125673	Not Available
3-Hydroxyisobutyric Aciduria	SMP0125674	Not Available
Isobutyryl-CoA Dehydrogenase Deficiency	SMP0125675	Not Available
Isovaleric Acidemia	SMP0125676	Not Available
Congenital Bile Acid Synthesis Defect Type II	SMP0125689	Not Available
Congenital Bile Acid Synthesis Defect Type III	SMP0125690	Not Available
Familial Hypercholanemia (FHCA)	SMP0125695	Not Available
Zellweger Syndrome	SMP0125696	Not Available
Cerebrotendinous Xanthomatosis (CTX)	SMP0125697	Not Available
Refsum Disease	SMP0125805	Not Available

Applications

Not Available

Biological Roles

metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.73 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	-5.2	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	176.83 m³·mol⁻¹	ChemAxon
Polarizability	72.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1921000110-a902ba2e846c5fa3a6f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-1911000000-73f7c171e662ee7ccd1d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-1910000000-e82bdc99f5bada8c440e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a7i-9830232560-d45384d1d1a3fe0dd614	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4910200000-2a67602fe8e4a74a6abe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-8900100000-d3e8a1b9393d73c218b4	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

In propionic aciduria, propionyl CoA accumulates within the mitochondria in massive quantities; free carnitine is then esterified, creating propionyl carnitine, which is then excreted in the urine. Because the supply of carnitine in the diet and from synthesis is limited, such patients readily develop carnitine deficiency as a result of the increased loss of acylcarnitine derivatives.

Metabolism

Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Propionic acidemia presents in the early neonatal period with progressive encephalopathy. Death can occur quickly, due to secondary hyperammonemia, infection, cardiomyopathy, or basal ganglial stroke. (Wikipedia)

Symptoms

Propionic acidemia is characterized almost immediately in newborns. Symptoms include poor feeding, vomiting, dehydration, acidosis, low muscle tone (hypotonia), seizures, and lethargy. The effects of propionic acidemia quickly become life-threatening. (Wikipedia)

Treatment

The carnitine deficiency associated with propionic acuduria demands supplementation of free carnitine above the normal dietary intake to continue to remove (detoxify) the accumulating organic acids.

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001275

FooDB ID

FDB022529

Phenol Explorer ID

Not Available

KNApSAcK ID