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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:02:47 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012552
Secondary Accession Numbers
  • HMDB12552
Metabolite Identification
Common Name12-Oxo-20-hydroxy-leukotriene B4
Description12-oxo-20-hydroxy-leukotriene B4 is the metabolite of lipid omega-oxidation of leukotriene B4 (LTB4). LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. The regulation of leukotriene production occurs at various levels, including expression of 5-LO, translocation of 5-LO to the perinuclear region, and phosphorylation to either enhance or inhibit the activity of 5-LO. Biologically active LTB4 is metabolized by omega-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the omega-carboxy position and after CoA ester formation (PMID: 7649996 , 17623009 , 2853166 , 6088485 ). Leukotrienes are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways.
Structure
Data?1582753064
Synonyms
ValueSource
(5S,20)-Dihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoateHMDB
(5S,20)-Dihydroxy-12-keto-(6Z,8E,10E,14Z)-eicosatetraenoic acidHMDB
(5S,20)-Dihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoateHMDB
(5S,20)-Dihydroxy-12-oxo-(6Z,8E,10E,14Z)-eicosatetraenoic acidHMDB
12-keto-20-Hydroxy-leukotriene b(,4)HMDB
Ox20hLTB4HMDB
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5R,6Z,8E,10E,14Z)-5,20-dihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
Traditional Name(5R,6Z,8E,10E,14Z)-5,20-dihydroxy-12-oxoicosa-6,8,10,14-tetraenoic acid
CAS Registry NumberNot Available
SMILES
OCCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,19,21,23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t19-/m0/s1
InChI KeyCZWPUWRHQBAXJS-PABROBRYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
Substituents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Keto fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Primary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.027 g/LALOGPS
logP3.48ALOGPS
logP3.1ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity104.02 m³·mol⁻¹ChemAxon
Polarizability39.84 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+195.23630932474
DeepCCS[M-H]-192.87830932474
DeepCCS[M-2H]-226.33130932474
DeepCCS[M+Na]+201.55830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12-Oxo-20-hydroxy-leukotriene B4OCCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@H](O)CCCC(O)=O4904.3Standard polar33892256
12-Oxo-20-hydroxy-leukotriene B4OCCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@H](O)CCCC(O)=O2711.9Standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4OCCCCC\C=C/CC(=O)\C=C\C=C\C=C/[C@H](O)CCCC(O)=O3222.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12-Oxo-20-hydroxy-leukotriene B4,1TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O3298.5Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,1TMS,isomer #2C[Si](C)(C)O[C@@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCCO)CCCC(=O)O3259.5Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,1TMS,isomer #3C[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=O)C/C=C\CCCCCO3200.7Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,1TMS,isomer #4C[Si](C)(C)OC(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)=C/C=C\CCCCCO3401.2Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C3351.9Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TMS,isomer #2C[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C3245.2Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TMS,isomer #3C[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C3442.0Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TMS,isomer #4C[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCCO)O[Si](C)(C)C3248.8Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TMS,isomer #5C[Si](C)(C)OC(/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C)=C/C=C\CCCCCO3434.9Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TMS,isomer #6C[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=C/C=C\CCCCCO)O[Si](C)(C)C3330.0Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3253.0Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TMS,isomer #2C[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3426.1Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TMS,isomer #3C[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3354.8Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TMS,isomer #4C[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=C/C=C\CCCCCO)O[Si](C)(C)C)O[Si](C)(C)C3374.4Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,4TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3372.4Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,4TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3131.0Standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,4TMS,isomer #1C[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3227.6Standard polar33892256
12-Oxo-20-hydroxy-leukotriene B4,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O3534.0Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCCO)CCCC(=O)O3493.4Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=O)C/C=C\CCCCCO3430.3Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)=C/C=C\CCCCCO3617.7Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C3813.2Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C3745.9Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O)O[Si](C)(C)C(C)(C)C3928.7Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=O)C/C=C\CCCCCO)O[Si](C)(C)C(C)(C)C3728.7Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)=C/C=C\CCCCCO3905.4Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC(=O)CCC[C@@H](O)/C=C\C=C\C=C\C(=C/C=C\CCCCCO)O[Si](C)(C)C(C)(C)C3836.3Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\CC(=O)/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4016.4Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4193.1Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@H](O)CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4135.8Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=O)CCC[C@H](/C=C\C=C\C=C\C(=C/C=C\CCCCCO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4131.9Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4377.9Semi standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3873.9Standard non polar33892256
12-Oxo-20-hydroxy-leukotriene B4,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCC/C=C\C=C(/C=C/C=C/C=C\[C@@H](CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3415.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-4496000000-330b9536066c0e39a5252017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 GC-MS (3 TMS) - 70eV, Positivesplash10-0ufr-7020970000-6960ae6f29e8dbf783f72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 10V, Positive-QTOFsplash10-00lr-0019000000-7e829671aaaf5a7306b72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 20V, Positive-QTOFsplash10-0159-1489000000-81410cfef5a26d2948fd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 40V, Positive-QTOFsplash10-00y3-7391000000-8808f7bc5690a3728c422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 10V, Negative-QTOFsplash10-000t-0009000000-96930ce14dbf697627522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 20V, Negative-QTOFsplash10-0f8a-1239000000-18615dcda9fe2a7b11602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 40V, Negative-QTOFsplash10-0a4l-9441000000-404df4ce49b0bb715d4f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 10V, Negative-QTOFsplash10-0002-0009000000-6e177b79bc05923f80972021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 20V, Negative-QTOFsplash10-0ku2-1229000000-afcf3b75c940869a28242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 40V, Negative-QTOFsplash10-0k96-5394000000-b002e38b9fda886421a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 10V, Positive-QTOFsplash10-00lr-0019000000-595b75883b13d52a09b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 20V, Positive-QTOFsplash10-0uyi-1239000000-d060f9437c01bc79e34e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Oxo-20-hydroxy-leukotriene B4 40V, Positive-QTOFsplash10-00fv-8933000000-48d2e616cbde56414f162021-09-24Wishart 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 IDFDB029119
KNApSAcK IDNot Available
Chemspider ID30776626
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481459
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wheelan P, Murphy RC: Metabolism of 6-trans-isomers of leukotriene B4 in cultured hepatoma cells and in human polymorphonuclear leukocytes. Identification of a delta 6-reductase metabolic pathway. J Biol Chem. 1995 Aug 25;270(34):19845-52. [PubMed:7649996 ]
  2. Murphy RC, Gijon MA: Biosynthesis and metabolism of leukotrienes. Biochem J. 2007 Aug 1;405(3):379-95. [PubMed:17623009 ]
  3. Mita H, Yui Y, Yasueda H, Shida T: Isocratic determination of arachidonic acid 5-lipoxygenase products in human neutrophils by high-performance liquid chromatography. J Chromatogr. 1988 Sep 9;430(2):299-308. [PubMed:2853166 ]
  4. Shak S, Goldstein IM: Omega-oxidation is the major pathway for the catabolism of leukotriene B4 in human polymorphonuclear leukocytes. J Biol Chem. 1984 Aug 25;259(16):10181-7. [PubMed:6088485 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.