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trans-octadec-2-enoyl-CoA (YMDB00470)

Identification
YMDB IDYMDB00470
Nametrans-octadec-2-enoyl-CoA
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTrans-2-octadecenoyl-CoA, also known as (e)-2-octadecenoyl-CoA, belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl). Thus, trans-2-octadecenoyl-CoA is considered to be a fatty ester lipid molecule. Trans-2-octadecenoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (2E)-Octadecenoyl-CoA
  • (2E)-Octadecenoyl-Coenzyme A
  • (E)-2-octadecenoyl-CoA
  • (E)-2-octadecenoyl-coenzyme A
  • (E)-octadec-2-enoyl-CoA
  • (E)-octadec-2-enoyl-coenzyme A
  • elaidic acid coenzyme a
  • trans-octadec-2-enoyl-CoA
  • trans-octadec-2-enoyl-coenzyme A
CAS numberNot Available
WeightAverage: 1031.98
Monoisotopic: 1031.360524011
InChI KeyNBCCUIHOHUKBMK-ZDDAFBBHSA-N
InChIInChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h18-19,26-28,32-34,38,49-50H,4-17,20-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b19-18+/t28-,32-,33-,34+,38-/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-[(2E)-octadec-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Nametrans-octadec-2-enoyl-coa
Chemical FormulaC39H68N7O17P3S
SMILESCCCCCCCCCCCCCCC\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
Description belongs to the class of organic compounds known as secondary carboxylic acid amides. Secondary carboxylic acid amides are compounds containing a secondary carboxylic acid amide functional group, with the general structure RC(=O)N(R')H (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassCarboxylic acid derivatives
Direct ParentSecondary carboxylic acid amides
Alternative Parents
Substituents
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP2.87ALOGPS
logP1.72ChemAxon
logS-3.1ALOGPS
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 Count35ChemAxon
Refractivity246.94 m³·mol⁻¹ChemAxon
Polarizability105.18 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
Biosynthesis of unsaturated fatty acidsPW002403 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (docosanoyl)PW002408 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (icosanoyl)PW002434 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (stearoyl)PW002435 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA)PW002404 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Biosynthesis of unsaturated fatty acidsec01040 Map01040
SMPDB Reactions
(3R)-3-hydroxy-stearoyl-CoA → trans-octadec-2-enoyl-CoA + water
trans-octadec-2-enoyl-CoA + hydron + NADPH → stearoyl-CoA + NADP
KEGG Reactions
3-hydroxyoctadecanoyl-CoA ↔ trans-octadec-2-enoyl-CoA + water
stearoyl-CoA + oxygen → trans-octadec-2-enoyl-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-3902020100-702c8c6bb21cd9180926JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913030000-9429405f3ae0c38fbca4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010100-0d3539439cc41d679212JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-9661431500-bb443918c6c1478b7d50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-4930210000-e27b2dee0f4b40981f33JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-09fe7ed24018a4548742JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-9000000000-cfe800ad5bbc58e06114JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-9010201300-6e87805c7ac31cddea17JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9102400305-4e9310c03d5744a7e414JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-23e10589819478bd138fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-4700100319-38af1792f0bfce070d96JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0100790000-0dd953635f26c9b0d42dJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID50570
HMDB IDHMDB06529
Pubchem Compound ID23724662
Kegg IDC16218
ChemSpider ID21865759
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD-10262

Enzymes

Protein Details
1. Acyl-coenzyme A oxidase
General function:
Involved in acyl-CoA dehydrogenase activity
Specific function:
Acyl-CoA + O(2) = trans-2,3-dehydroacyl-CoA + H(2)O(2)
Gene Name:
POX1
Uniprot ID:
P13711
Molecular weight:
84041.39844
Reactions
Acyl-CoA + O(2) → trans-2,3-dehydroacyl-CoA + H(2)O(2).
Protein Details
2. Peroxisomal hydratase-dehydrogenase-epimerase
General function:
Involved in oxidoreductase activity
Specific function:
Second trifunctional enzyme acting on the beta-oxidation pathway for fatty acids, possessing hydratase-dehydrogenase- epimerase activities. Converts trans-2-enoyl-CoA via D-3- hydroxyacyl-CoA to 3-ketoacyl-CoA
Gene Name:
FOX2
Uniprot ID:
Q02207
Molecular weight:
98702.39844
Reactions
(3R)-3-hydroxyacyl-CoA → (2E)-2-enoyl-CoA + H(2)O.
(R)-3-hydroxyacyl-CoA + NAD(+) → 3-oxoacyl-CoA + NADH.
Protein Details
3. Enoyl-[acyl-carrier protein] reductase [NADPH, B-specific], mitochondrial
General function:
Involved in zinc ion binding
Specific function:
Required for respiration and the maintenance of the mitochondrial compartment. May have a role in the mitochondrial synthesis of fatty acids
Gene Name:
ETR1
Uniprot ID:
P38071
Molecular weight:
42066.5
Reactions
Acyl-[acyl-carrier-protein] + NADP(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADPH.
Acyl-CoA + NADP(+) → trans-2,3-dehydroacyl-CoA + NADPH.