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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-16 22:36:33 UTC
Update Date2021-09-14 15:43:09 UTC
HMDB IDHMDB0011123
Secondary Accession Numbers
  • HMDB11123
Metabolite Identification
Common Nametrans,cis-Lauro-2,6-dienoyl-CoA
DescriptionTrans,cis-Lauro-2,6-dienoyl-CoA is a co-enzyme A intermediate that participates in fatty acid metabolism, especially long chain fatty acid biosynthesis. trans,cis-Lauro-2,6-dienoyl-CoA is converted from cis,cis-3,6-Dodecadienoyl-CoA via the enzyme known as dodecenoyl-CoA delta-isomerase [EC:5.3.3.8] and vice-versa. Fatty acid degradation is the process in which fatty acids are broken down, resulting in release of energy. It includes three major steps: Activation and transport into mitochondria, β-oxidation and movement through the electron transport chain. Fatty acids are transported across the outer mitochondrial membrane by carnitine-palmitoyl transferase I (CPT-I), and then couriered across the inner mitochondrial membrane by carnitine (PMID:11413487 ). Once inside the mitochondrial matrix, fatty acyl-carnitine reacts with coenzyme A to release the fatty acid and produce acetyl-CoA. CPT-I is believed to be the rate limiting step in fatty acid oxidation. Once inside the mitochondrial matrix, fatty acids undergo β-oxidation (PMID: 25703630 ). During this process, two-carbon molecules (in the form of acetyl-CoA) are repeatedly cleaved from the fatty acid. Acetyl-CoA can then enter the TCA cycle, which produces NADH and FADH. NADH and FADH are subsequently used in the electron transport chain to produce ATP, the energy currency of the cell.
Structure
Data?1582752870
SynonymsNot Available
Chemical FormulaC33H54N7O17P3S
Average Molecular Weight945.805
Monoisotopic Molecular Weight945.250973563
IUPAC Name{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-{[2-({2-[(2E,5Z)-dodeca-2,5-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3R,5R)-5-(6-aminopurin-9-yl)-2-[({[(3R)-3-{[2-({2-[(2E,5Z)-dodeca-2,5-dienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCC\C=C/C\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
InChI Identifier
InChI=1S/C33H54N7O17P3S/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/h9-10,12-13,20-22,26-28,32,43-44H,4-8,11,14-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/b10-9-,13-12+/t22-,26?,27+,28+,32-/m1/s1
InChI KeyZSJRXHRCABOSNC-XRUZZFSQSA-N
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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.75 g/LALOGPS
logP10(1.51) g/LALOGPS
logP10(-2.4) g/LChemAxon
logS10(-2.7) g/LALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count28ChemAxon
Refractivity220.45 m³·mol⁻¹ChemAxon
Polarizability90.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 10V, Positive-QTOFsplash10-000i-1911100101-e5f10534962f5126333b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 20V, Positive-QTOFsplash10-000i-0931300000-e61d0a602c5b72d1498d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 40V, Positive-QTOFsplash10-000i-1900100000-7e810f634fe0a18fe74d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 10V, Negative-QTOFsplash10-0059-2922031304-fb5f3967b6363fef722a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 20V, Negative-QTOFsplash10-003r-3901110000-e512fb641f2ee1e2aedd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 40V, Negative-QTOFsplash10-057i-5900000000-483ce48063010b609c0a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 10V, Negative-QTOFsplash10-0006-0000000009-9443e91378915a9f93122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 20V, Negative-QTOFsplash10-002f-4200302409-7c7420ee136b22e6e4942021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 40V, Negative-QTOFsplash10-017i-2101301903-88a619f1eda2f67f51292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 10V, Positive-QTOFsplash10-0002-0000000019-47710a6512802c8ac5742021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 20V, Positive-QTOFsplash10-000i-2901000454-d5c1019cb5d3fe7955562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans,cis-Lauro-2,6-dienoyl-CoA 40V, Positive-QTOFsplash10-000i-0002900000-c40f7453a0645cbbf3cc2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027905
KNApSAcK IDNot Available
Chemspider ID59683988
KEGG Compound IDC05279
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53480665
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDC05279
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Shi L, Tu BP: Acetyl-CoA and the regulation of metabolism: mechanisms and consequences. Curr Opin Cell Biol. 2015 Apr;33:125-31. doi: 10.1016/j.ceb.2015.02.003. Epub 2015 Feb 20. [PubMed:25703630 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
EHHADH
Uniprot ID:
Q08426
Molecular weight:
69153.26
Reactions
cis,cis-3,6-Dodecadienoyl-CoA → trans,cis-Lauro-2,6-dienoyl-CoAdetails
General function:
Involved in catalytic activity
Specific function:
Able to isomerize both 3-cis and 3-trans double bonds into the 2-trans form in a range of enoyl-CoA species.
Gene Name:
ECI1
Uniprot ID:
P42126
Molecular weight:
30895.4
Reactions
cis,cis-3,6-Dodecadienoyl-CoA → trans,cis-Lauro-2,6-dienoyl-CoAdetails
General function:
Involved in acyl-CoA binding
Specific function:
Able to isomerize both 3-cis and 3-trans double bonds into the 2-trans form in a range of enoyl-CoA species. Has a preference for 3-trans substrates (By similarity).
Gene Name:
ECI2
Uniprot ID:
O75521
Molecular weight:
40182.735
Reactions
cis,cis-3,6-Dodecadienoyl-CoA → trans,cis-Lauro-2,6-dienoyl-CoAdetails