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(2E)-Dodecenoyl-CoA (YMDB00215)

Identification
YMDB IDYMDB00215
Name(2E)-Dodecenoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(2E)-Dodecenoyl-CoA, also known as (2E)-dodec-2-enoyl-CoA or 2-trans-dodecenoyl-CoA, 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. Based on a literature review very few articles have been published on (2E)-Dodecenoyl-CoA.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2E)-Dodec-2-enoyl-CoA
  • (2E)-Dodec-2-enoyl-Coenzyme A
  • 2-trans-Dodecenoyl-CoA
  • 2-trans-Dodecenoyl-Coenzyme A
  • (2E)-Dodecenoyl-CoA
CAS number1066-12-2
WeightAverage: 947.821
Monoisotopic: 947.266623627
InChI KeyIRFYVBULXZMEDE-DEEZISNZSA-N
InChIInChI=1S/C33H56N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h12-13,20-22,26-28,32,43-44H,4-11,14-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/b13-12+/t22-,26-,27-,28+,32-/m1/s1
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(2E)-dodec-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 Nametrans-dodec-2-enoyl-coa
Chemical FormulaC33H56N7O17P3S
SMILESCCCCCCCCC\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=C(N)N=CN=C12
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentMedium-chain 2-enoyl 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
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP0.519PhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.3 g/LALOGPS
logP1.41ALOGPS
logP-0.95ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count29ChemAxon
Refractivity219.34 m³·mol⁻¹ChemAxon
Polarizability90.65 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • lipid particle
  • endoplasmic reticulum
  • peroxisome
Organoleptic PropertiesNot Available
SMPDB Pathways
Fatty acid elongation in mitochondriaPW002467 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid metabolismPW002460 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid elongation in mitochondriaec00062 Map00062
Fatty acid metabolismec00071 Map00071
SMPDB Reactions
(S)-3-hydroxylauroyl-CoA ↔ (2E)-Dodecenoyl-CoA + water
(2E)-Dodecenoyl-CoA + NADPH → lauroyl-CoA + NADP
KEGG Reactions
(S)-3-hydroxylauroyl-CoA ↔ (2E)-Dodecenoyl-CoA + water
lauroyl-CoA + oxygen → (2E)-Dodecenoyl-CoA + Hydrogen peroxide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1945000202-3935b90e93f42c57c383JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0963100000-76e7d2ecf42a69de257fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1931000000-0a31c1caf454ec14312bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-3911032304-f163cfb1d8b6995c8f24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-2900110001-7ef123400b090afe0b26JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-7900000000-349d97519ce451369a61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000000019-58bf1dfa7c94908bff4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1901000456-82b2f81fe92b050b4cdbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0001900000-07c324a5e8565c914e97JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000000009-983824b3dc4935215fdaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-4200302409-0c27a425d05507057591JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00p0-3302501906-4e51e92e28749536f9b4JSpectraViewer
MSMass Spectrum (Electron Ionization)Not AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Struijk, Cornelia B.; Beerthuis, R. K. The enzymic conversion of 3cis-and 3trans-alkenoyl-CoA esters into their 2trans-isomers. Biochimica et Biophysica Acta, Lipids and Lipid Metabolism (1966), 116(1), 12-22.
External Links:
ResourceLink
CHEBI ID15471
HMDB IDHMDB03712
Pubchem Compound ID5280578
Kegg IDC03221
ChemSpider ID10140104
FOODB IDFDB030364
Wikipedia IDNot Available
BioCyc IDCPD-7222

Enzymes

Protein Details
1. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA. Has an indirect role in endocytic membrane trafficking. May have a function in protein biosynthesis in mitochondrial small ribosomal subunit
Gene Name:
EHD3
Uniprot ID:
P28817
Molecular weight:
56287.89844
Reactions
3-hydroxy-2-methylpropanoyl-CoA + H(2)O → CoA + 3-hydroxy-2-methylpropanoate.
Protein Details
2. 3-ketoacyl-CoA thiolase, peroxisomal
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyl-CoA + acetyl-CoA = CoA + 3-oxoacyl-CoA
Gene Name:
POT1
Uniprot ID:
P27796
Molecular weight:
44729.89844
Reactions
Acyl-CoA + acetyl-CoA → CoA + 3-oxoacyl-CoA.
Protein Details
3. 3,2-trans-enoyl-CoA isomerase
General function:
Involved in catalytic activity
Specific function:
Essential for the beta oxidation of unsaturated fatty acids
Gene Name:
ECI1
Uniprot ID:
Q05871
Molecular weight:
31698.09961
Reactions
(3Z)-dodec-3-enoyl-CoA → (2E)-dodec-2-enoyl-CoA.