Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000544
Name: (2E)-Octenoyl-CoA
Description:(2E)-Octenoyl-CoA is the main metabolite produced in medium-chain acyl-CoA dehydrogenase (EC, MCAD) deficiency; however the product of the enzymatic reaction is not directly detected in several methods for screening of inborn errors of fatty acid oxidation. In order to aid the timely follow-up of screening results that suggest abnormalities in MCAD, rapid and simple confirmatory tests for the enzyme activity and/or gene mutation analysis should be available.
  • (E)-S-2-octenoate
  • (E)-S-2-octenoate CoA
  • (E)-S-2-octenoate Coenzyme A
  • (E)-S-2-octenoic acid
  • (E)-S-2-octenoic acid CoA
  • (E)-S-2-octenoic acid Coenzyme A
  • 2,3-trans-Octenoyl coenzyme A
  • Oct-2-trans-enoyl-CoA
  • Oct-2-trans-enoyl-Coenzyme A
  • Oct-trans-2-enoyl coenzyme A
  • S-(2E)-2-Octenoate
  • S-(2E)-2-Octenoate CoA
  • S-(2E)-2-Octenoate Coenzyme A
  • S-(2E)-2-Octenoic acid
  • S-(2E)-2-Octenoic acid CoA
  • S-(2E)-2-Octenoic acid Coenzyme A
  • Trans-D2,3-Octenoyl-CoA
  • Trans-D2,3-Octenoyl-Coenzyme A
  • Trans-Oct-2-enoyl-CoA
  • Trans-Oct-2-enoyl-Coenzyme A
Chemical Formula: C29H48N7O17P3S
Average Molecular Weight: 891.714
Monoisotopic Molecular Weight: 891.204023371
CAS number: 10018-94-7
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-[(2E)-oct-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(2E)-oct-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent Medium-chain 2-enoyl CoAs
Alternative Parents
  • 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
  • Saccharide
  • 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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: Not Available
Experimental Properties:
Predicted Properties
Water Solubility3.13 mg/mLALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count25ChemAxon
Refractivity200.93 m3·mol-1ChemAxon
Polarizability81.26 Å3ChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1912000120-6a4c400b3152685ddc42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0933000000-6bfba9e629e0c41c1c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1911000000-7bd78cc2705414ac12aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00gl-3911030340-0a6b8d53ed19f026db3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ai-3910010010-8cc155429b1ae945edc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-8852cd72aadbe50cd70bView in MoNA
  • Cummings JG, Lau SM, Powell PJ, Thorpe C: Reductive half-reaction in medium-chain acyl-CoA dehydrogenase: modulation of internal equilibrium by carboxymethylation of a specific methionine residue. Biochemistry. 1992 Sep 15;31(36):8523-9. Pubmed: 1390638
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Kumar NR, Srivastava DK: Reductive half-reaction of medium-chain fatty acyl-CoA dehydrogenase utilizing octanoyl-CoA/octenoyl-CoA as a physiological substrate/product pair: similarity in the microscopic pathways of octanoyl-CoA oxidation and octenoyl-CoA binding. Biochemistry. 1994 Jul 26;33(29):8833-41. Pubmed: 8038175
  • Tajima G, Sakura N, Yofune H, Nishimura Y, Ono H, Hasegawa Y, Hata I, Kimura M, Yamaguchi S, Shigematsu Y, Kobayashi M: Enzymatic diagnosis of medium-chain acyl-CoA dehydrogenase deficiency by detecting 2-octenoyl-CoA production using high-performance liquid chromatography: a practical confirmatory test for tandem mass spectrometry newborn screening in Japan. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Sep 5;823(2):122-30. Pubmed: 16046200
Synthesis Reference: Reiser, S. E.; Gruys, K. J.; Mitsky, T. A. Characterization and cloning of an (R)-specific trans-2,3-enoylacyl-CoA hydratase from Rhodospirillum rubrum and use of this enzyme for PHA production in Escherichia coli. Applied Microbiology and Biotechnolo
Material Safety Data Sheet (MSDS) Not Available
External Links:
Pubchem Compound ID5280769
Kegg IDC05276
ChemSpider ID4444335
Wikipedia IDNot Available
BioCyc IDNot Available