propionyl-CoA (YMDB00446)

Identification

YMDB ID

YMDB00446

Name

propionyl-CoA

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Propanoyl-CoA, also known as S-propanoyl-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. Thus, propanoyl-CoA is considered to be a fatty ester lipid molecule. Propanoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-methylacetyl-CoA
2-methylacetyl-Coenzyme A
alpha-methylacetyl-CoA
alpha-methylacetyl-Coenzyme A
n-propionyl-CoA
n-propionyl-coenzyme A
propanoyl-CoA
propanoyl-Coenzyme A
propionyl coenzyme a
Propionyl-CoA
propionyl-coenzyme A
S-Propionyl-coenzym-A
S-Propionylcoenzyme A
S-Propanoyl-CoA
S-Propanoyl-coenzyme A
Propionyl CoA
n-Propionyl CoA

CAS number

317-66-8

Weight

Average: 823.597
Monoisotopic: 823.141423115

InChI Key

QAQREVBBADEHPA-IEXPHMLFSA-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

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

Chemical Formula

C₂₄H₄₀N₇O₁₇P₃S

SMILES

CCC(=O)SCCNC(=O)CCNC(=O)[C@H](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

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Imidolactam
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Thiocarboxylic acid ester
Secondary alcohol
Amino acid or derivatives
Carbothioic s-ester
Thiocarboxylic acid or derivatives
Sulfenyl compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid derivative
Organic 1,3-dipolar compound
Organoheterocyclic compound
Azacycle
Oxacycle
Organopnictogen compound
Organic oxygen compound
Organic oxide
Amine
Hydrocarbon derivative
Primary amine
Carbonyl group
Alcohol
Organosulfur compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl-CoA (CHEBI:15539 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	4.27 g/L	ALOGPS
logP	-0.31	ALOGPS
logP	-5.2	ChemAxon
logS	-2.3	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	74.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

mitochondrion
lipid particle
endoplasmic reticulum

Organoleptic Properties

Not Available

SMPDB Pathways

beta-Alanine metabolism

PW002381

KEGG Pathways

Glycerolipid metabolism	ec00561
Glyoxylate and dicarboxylate metabolism	ec00630
Propanoate metabolism	ec00640
Valine, leucine and isoleucine degradation	ec00280
beta-Alanine metabolism	ec00410

SMPDB Reactions

Not Available

KEGG Reactions

propionyl-CoA + water + Oxalacetic acid → (2S,3S)-2-Methylcitric acid + hydron + Coenzyme A

NAD + Coenzyme A + 2-Ketobutyric acid → NADH + propionyl-CoA + Carbon dioxide

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1901000220-8d8b91979e9c40176540	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0912000000-7c91e2c2f2f0d7b4a3ad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2901000000-4311d5cc2b23055e1e3e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a7i-9830230550-4bec7e3f4052a0f39eef	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0560-4910100000-d7281a44fcd4120a6bcd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-19dd2ec65951d55b39f7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000190-23b4b60665f8f21035f9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-9000000000-6406a938fedabc06792a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kr-7003503900-84f2f16540c6fdc2e156	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000090-c1703348da5a9b18dd37	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1911003540-d00d30c93f6f200af707	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0129000000-299d7589b9a24abdcb95	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Pronk, J. T., van der Linden-Beuman, A., Verduyn, C., Scheffers, W. A., van Dijken, J. P. (1994). "Propionate metabolism in Saccharomyces cerevisiae: implications for the metabolon hypothesis." Microbiology 140 ( Pt 4):717-722.7912143
Singh, J., Kumar, D., Ramakrishnan, N., Singhal, V., Jervis, J., Garst, J. F., Slaughter, S. M., DeSantis, A. M., Potts, M., Helm, R. F. (2005). "Transcriptional response of Saccharomyces cerevisiae to desiccation and rehydration." Appl Environ Microbiol 71:8752-8763.16332871

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.

External Links:

Resource	Link
CHEBI ID	15539
HMDB ID	HMDB01275
Pubchem Compound ID	439164
Kegg ID	C00100
ChemSpider ID	24784993
FOODB ID	FDB022529
Wikipedia	Propionyl-CoA
BioCyc ID	PROPIONYL-COA

Enzymes

Protein Details

1. Acetyl-coenzyme A synthetase 1

General function:: Involved in acetate-CoA ligase activity
Specific function:: Catalyzes the production of acetyl-CoA. Provides the acetyl-CoA source for histone acetylation in the nucleus. "Aerobic" isozyme of acetyl-coenzyme A synthetase, which supports growth on nonfermentable carbon sources such as glycerol and ethanol. May be required for assimilation of ethanol and acetate
Gene Name:: ACS1
Uniprot ID:: Q01574
Molecular weight:: 79140.10156

Reactions

ATP + acetate + CoA → AMP + diphosphate + acetyl-CoA.

Protein Details

2. Acetyl-coenzyme A synthetase 2

General function:: Involved in acetate-CoA ligase activity
Specific function:: Catalyzes the production of acetyl-CoA. Provides the acetyl-CoA source for histone acetylation in the nucleus. "Anaerobic" isozyme of acetyl-coenzyme A synthetase, which is required for growth on fermentable carbon sources such as glucose. May be involved in the PDH (pyruvate dehydrogenase complex) bypass
Gene Name:: ACS2
Uniprot ID:: P52910
Molecular weight:: 75491.10156

Reactions

ATP + acetate + CoA → AMP + diphosphate + acetyl-CoA.

Protein Details

3. Citrate synthase 3

General function:: Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:: Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA
Gene Name:: CIT3
Uniprot ID:: P43635
Molecular weight:: 53810.69922

Reactions

Acetyl-CoA + H(2)O + oxaloacetate → citrate + CoA.
propanoyl-CoA + H2O + oxaloacetate → (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA

Protein Details

4. N-acetyltransferase HPA3

General function:: Involved in N-acetyltransferase activity
Specific function:: N-acetyltransferase whose physiological acetyl acceptor substrate is still unknown. In vitro, histone acetylation is very weak
Gene Name:: HPA3
Uniprot ID:: P39979
Molecular weight:: 20698.5

Reactions

acetyl-CoA + a D-amino acid → CoA + an N-acetyl-D-amino acid

Structure for #<Compound:0xa01415a4>

Enzymes

Reactions

Reactions

Reactions

Reactions