Trans-Octadec-2-enoyl-CoA (PAMDB001759)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001759
Identification
Name: Trans-Octadec-2-enoyl-CoA
Description:trans-Octadec-2-enoyl-CoA is an intermediate in Biosynthesis of unsaturated fatty acids. trans-Octadec-2-enoyl-CoA is produced from 3-Hydroxyoctadecanoyl-CoA and then converted to Stearoyl-CoA via enzymatic reaction.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • (2E)-octadecenoyl-CoA
  • (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
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulfanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-({3-[(2-{[(2E)-octadec-2-enoyl]sulphanyl}ethyl)amino]-3-oxopropyl}amino)-4-oxobutyl] dihydrogen diphosphoric acid}
  • trans-2,3-dihydro-stearenoyl-CoA
  • Elaidate coenzyme a
  • Elaidic acid coenzyme a
  • Trans-2,3-Dihydro-stearenoyl-CoA
  • Trans-Octadec-2-enoyl-CoA
  • Trans-Octadec-2-enoyl-coenzyme A
Chemical Formula: C39H68N7O17P3S
Average Molecular Weight: 1031.98
Monoisotopic Molecular Weight: 1031.360524011
InChI Key: NBCCUIHOHUKBMK-XCRBYWPRSA-N
InChI:InChI=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
CAS number: Not Available
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 Name: trans-octadec-2-enoyl-coa
SMILES:CCCCCCCCCCCCCCC\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(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
  • 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
Predicted Properties
PropertyValueSource
Water Solubility0.816 mg/mLALOGPS
logP2.87ALOGPS
logP0.63ChemAxon
logS-3.1ALOGPS
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 Count35ChemAxon
Refractivity246.94 m3·mol-1ChemAxon
Polarizability104.1 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
(S)-3-Hydroxyoctadecanoyl-CoA <> Water + Trans-Octadec-2-enoyl-CoA
FAD + Stearoyl-CoA <> FADH2 + Trans-Octadec-2-enoyl-CoA
Octadecenoyl-CoA (N-C18:1CoA) <> Trans-Octadec-2-enoyl-CoA
trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA > (S)-3-Hydroxyoctadecanoyl-CoA + Water
(S)-3-Hydroxyoctadecanoyl-CoA > trans-Octadec-2-enoyl-CoA + Trans-Octadec-2-enoyl-CoA
trans-Octadec-2-enoyl-CoA + Water + Trans-Octadec-2-enoyl-CoA > Coenzyme A + Hydrogen ion + Elaidic acid
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3902020100-702c8c6bb21cd9180926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0913030000-9429405f3ae0c38fbca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010100-0d3539439cc41d679212View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-9661431500-bb443918c6c1478b7d50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01si-4930210000-e27b2dee0f4b40981f33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900000000-09fe7ed24018a4548742View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID50570
HMDB IDHMDB06529
Pubchem Compound ID23724662
Kegg IDC16218
ChemSpider ID21865759
Wikipedia IDNot Available
BioCyc IDCPD-10262
EcoCyc IDCPD-10262

Enzymes

Protein Details
• Fatty acid oxidation complex subunit alpha
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.
Protein Details
• Acyl-coenzyme A dehydrogenase
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).
Protein Details
• Acyl-CoA thioesterase 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