Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB000541
Identification
Name: (2E)-Hexadecenoyl-CoA
Description:(2E)-Hexadecenoyl-CoA is an intermediate in fatty acid metabolism, the substrate of the enzyme enoyl-CoA hydratase [EC:4.2.1.17]. It is also the substrate of the enzyme trans-2-enoyl-CoA reductase [EC:1.3.1.38], in fatty acid elongation. (PMID: 1278159, KEGG)
Structure
Thumb
Synonyms:
  • (2E)-Hexadecenoyl-CoA
  • (2E)-Hexadecenoyl-Coenzyme A
  • Trans-2-Hexadecenoyl-CoA
  • Trans-2-Hexadecenoyl-Coenzyme A
Chemical Formula: C37H60N7O17P3S
Average Molecular Weight: 999.895
Monoisotopic Molecular Weight: 999.297923755
InChI Key: JUPAQFRKPHPXLD-MSHHSVQMSA-J
InChI:InChI=1S/C37H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-28(46)65-21-20-39-27(45)18-19-40-35(49)32(48)37(2,3)23-58-64(55,56)61-63(53,54)57-22-26-31(60-62(50,51)52)30(47)36(59-26)44-25-43-29-33(38)41-24-42-34(29)44/h16-17,24-26,30-32,36,47-48H,4-15,18-23H2,1-3H3,(H,39,45)(H,40,49)(H,53,54)(H,55,56)(H2,38,41,42)(H2,50,51,52)/p-4/b17-16+/t26-,30-,31-,32+,36-/m1/s1
CAS number: 4460-95-1
IUPAC Name:(3R)-3-{[2-({2-[(2E)-hexadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropyl ({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
Traditional IUPAC Name: (E)-hexadec-2-enoyl-coa(4-)
SMILES:CCCCCCCCCCCCC\C=C\C(=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
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent Long-chain 2-enoyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • 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
  • 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
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:2.319PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP3.34ALOGPS
logP-0.26ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area374.95 Å2ChemAxon
Rotatable Bond Count33ChemAxon
Refractivity233.25 m3·mol-1ChemAxon
Polarizability98.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-9000000100-a1fa399e8b9a0f5a7be2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-9105020007-451c96f9724068202e5aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-8915200100-0a7f3c9c09ea57c0b387View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3000000009-b59c42d14785cf69a6d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-6090200005-6be90b350179fc9c49c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01si-9700110000-b7c4f7cab1d1a272cd4bView in MoNA
References
References:
  • Hinsch, W., Klages, C., Seubert, W. (1976). "On the mechanism of malonyl-CoA-independent fatty-acid synthesis. Different properties of the mitochondrial chain elongation and enoylCoA reductase in various tissues." Eur J Biochem 64:45-55. Pubmed: 1278159
  • 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
Synthesis Reference: Al-Arif, Adhid; Blecher, Melvin. Chemical synthesis of carnitine and coenzyme A esters of the b-substituted intermediates of hexadecanoic acid metabolism. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1971), 248(3), 416-29.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID28935
HMDB IDHMDB03945
Pubchem Compound ID5280766
Kegg IDC05272
ChemSpider ID26332261
Wikipedia IDNot Available
BioCyc IDCPD0-2117
EcoCyc IDCPD0-2117

Enzymes

General function:
Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:
Catalyzes the formation of an hydroxyacyl-CoA by addition of water on enoyl-CoA. Also exhibits 3-hydroxyacyl-CoA epimerase and 3-hydroxyacyl-CoA dehydrogenase activities. Involved in the aerobic and anaerobic degradation of long-chain fatty acids
Gene Name:
fadB
Locus Tag:
PA3014
Molecular weight:
77 kDa
Reactions
(S)-3-hydroxyacyl-CoA + NAD(+) = 3-oxoacyl-CoA + NADH.
(3S)-3-hydroxyacyl-CoA = trans-2(or 3)-enoyl-CoA + H(2)O.
(S)-3-hydroxybutanoyl-CoA = (R)-3-hydroxybutanoyl-CoA.
(3Z)-dodec-3-enoyl-CoA = (2E)-dodec-2-enoyl-CoA.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the esterification, concomitant with transport, of exogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids
Gene Name:
fadD
Locus Tag:
PA3299
Molecular weight:
61.7 kDa
Reactions
ATP + a long-chain fatty acid + CoA = AMP + diphosphate + an acyl-CoA.
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Catalyzes the dehydrogenation of acyl-CoA
Gene Name:
fadE
Locus Tag:
PA2815
Molecular weight:
88.8 kDa
Reactions
An acyl-CoA + FAD = a dehydrogenated acyl-CoA + FADH(2).
General function:
Involved in acyl-CoA hydrolase activity
Specific function:
Can hydrolyze a broad range of acyl-CoA thioesters. Its physiological function is not known
Gene Name:
tesB
Locus Tag:
PA3942
Molecular weight:
32.9 kDa