Canmetcon
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Identification
YMDB IDYMDB00446
Namepropionyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPropionyl-CoA is a coenzyme A derivative of propionic acid. There are several different ways in which it is formed: 1) as a product of beta-oxidation of odd-chain fatty acids, 2) as a product of metabolism of isoleucine and valine or, 3) as a product of alpha-ketobutyric acid, which in turn is a product of threonine and methionine metabolism. [Wikipidia]
Structure
Thumb
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
CAS number317-66-8
WeightAverage: 823.597
Monoisotopic: 823.141423115
InChI KeyQAQREVBBADEHPA-IEXPHMLFSA-N
InChIInChI=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 Namepropionyl-coa
Chemical FormulaC24H40N7O17P3S
SMILESCCC(=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
DescriptionThis compound 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 diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.27 g/LALOGPS
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
Polarizability73.8 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • lipid particle
  • endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB Pathways
beta-Alanine metabolismPW002381 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
Glyoxylate and dicarboxylate metabolismec00630 Map00630
Propanoate metabolismec00640 Map00640
Valine, leucine and isoleucine degradationec00280 Map00280
beta-Alanine metabolismec00410 Map00410
SMPDB ReactionsNot Available
KEGG Reactions
propionyl-CoA + water + Oxalacetic acid(2S,3S)-2-Methylcitric acid + hydron + Coenzyme A
NAD + Coenzyme A + 2-Ketobutyric acidNADH + propionyl-CoA + Carbon dioxide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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:
ResourceLink
CHEBI ID15539
HMDB IDHMDB01275
Pubchem Compound ID439164
Kegg IDC00100
ChemSpider ID24784993
FOODB IDNot Available
WikipediaPropionyl-CoA
BioCyc IDPROPIONYL-COA

Enzymes

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.
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.
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
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