trans-2-Hexenoyl-CoA (PAMDB000540)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000540
Identification
Name: trans-2-Hexenoyl-CoA
Description:Trans-Hexenoyl-CoA is an intermediate in fatty acid metabolism. trans-Hexenoyl-CoA is the substrate of the enzymes enoyl-coenzyme A reductase, acyl-CoA oxidase [EC 1.3.99.2-1.3.3.6], acyl-CoA dehydrogenase, long-chain-acyl-CoA dehydrogenase [EC 1.3.99.3-1.3.99.13], and Oxidoreductases [EC 1.3.99.-]; It is an intermediate in fatty acid elongation, being the substrate of the enzymes enoyl-CoA hydratase and long-chain-enoyl-CoA hydratase [EC 4.2.1.17-4.2.1.74].
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2E)-hexenoyl-CoA
  • (2E)-Hexenoyl-CoA
  • (2E)-Hexenoyl-Coenzyme A
  • trans-2-hexenoyl-CoA
  • Hexenoyl-CoA
  • Trans-2,3-Dehydrohexanoyl-CoA
  • Trans-2,3-Dehydrohexanoyl-Coenzyme A
  • Trans-Hex-2-enoyl-CoA
  • Trans-Hex-2-enoyl-Coenzyme A
Chemical Formula: C27H44N7O17P3S
Average Molecular Weight: 863.661
Monoisotopic Molecular Weight: 863.172723243
InChI Key: OINXHIBNZUUIMR-DOSZRKKKSA-N
InChI:InChI=1S/C27H44N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h6-7,14-16,20-22,26,37-38H,4-5,8-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/b7-6+/t16-,20-,21-,22?,26-/m1/s1
CAS number: 10018-93-6
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-hex-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(2E)-hex-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid
SMILES:CCC\C=C\C(=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
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
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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.181PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.54 mg/mLALOGPS
logP0.17ALOGPS
logP-4.7ChemAxon
logS-2.4ALOGPS
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 Count23ChemAxon
Refractivity191.73 m3·mol-1ChemAxon
Polarizability77.19 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
(S)-Hydroxyhexanoyl-CoA <> Water + trans-2-Hexenoyl-CoA
FAD + Hexanoyl-CoA <> FADH2 + trans-2-Hexenoyl-CoA
Hexanyl-CoA + electron-transfer flavoprotein > trans-2-Hexenoyl-CoA + Reduced electron-transfer flavoprotein
trans-2-Hexenoyl-CoA < (S)-Hydroxyhexanoyl-CoA
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1902000120-12f3a35f3f9ab291ff00View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1912000000-1f13bbf987a235864a7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2911000000-9a6ce611452163aa9b91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01sm-8930140550-852eb909c02343edb382View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-6910010010-97a6c041da0e77ec8644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-06a3c53b188324acdb55View in MoNA
References
References:
  • 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
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Reddy, J. K., Hashimoto, T. (2001). "Peroxisomal beta-oxidation and peroxisome proliferator-activated receptor alpha: an adaptive metabolic system." Annu Rev Nutr 21:193-230. Pubmed: 11375435
Synthesis Reference: Tamvakopoulos, Constantine S.; Anderson, Vernon E. Detection of acyl-coenzyme A thioester intermediates of fatty acid b-oxidation as the N-acylglycines by negative-ion chemical ionization gas chromatography mass spectrometry. Analytical Biochemistry
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28706
HMDB IDHMDB03944
Pubchem Compound ID5280765
Kegg IDC05271
ChemSpider ID4444331
Wikipedia IDNot Available
BioCyc IDCPD0-2121
EcoCyc IDCPD0-2121