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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 15:39:02 UTC
HMDB IDHMDB0014687
Secondary Accession Numbers
  • HMDB14687
Metabolite Identification
Common NameDesoximetasone
DescriptionDesoximetasone is only found in individuals that have used or taken this drug. It is a topical anti-inflammatory glucocorticoid used in dermatoses, skin allergies, psoriasis, etc. [PubChem]The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. This is achieved first by the drug binding to the glucocorticoid receptors which then translocates into the nucleus and binds to DNA causing various activations and repressions of genes. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.
Structure
Data?1582753209
Synonyms
ValueSource
(11beta,16alpha)-9-Fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dioneChEBI
9alpha-Fluoro-16alpha-methyl-Delta(1)-corticosteroneChEBI
DesoximetasonaChEBI
DesoximetasonumChEBI
DesoxymethasoneChEBI
TopicortKegg
(11b,16a)-9-Fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dioneGenerator
(11Β,16α)-9-fluoro-11,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dioneGenerator
9a-Fluoro-16a-methyl-delta(1)-corticosteroneGenerator
9Α-fluoro-16α-methyl-δ(1)-corticosteroneGenerator
9a-Fluoro-16a-methyl-δ(1)-corticosteroneHMDB
DesoxiHMDB
Hoechst brand OF desoximetasoneHMDB
IbarilHMDB
Optipharma brand OF desoximetasoneHMDB
TopicorteHMDB
TopisolonHMDB
17-DesoxymethasoneHMDB
Abbott brand OF desoximetasoneHMDB
Medicis brand OF desoximetasoneHMDB
StiedexHMDB
17 DesoxymethasoneHMDB
DeoxydexamethasoneHMDB
Dermik brand OF desoximetasoneHMDB
Stiefel brand OF desoximetasoneHMDB
Aventis brand OF desoximetasoneHMDB
Bipharma brand OF desoximetasoneHMDB
FlubasonHMDB
Chemical FormulaC22H29FO4
Average Molecular Weight376.4617
Monoisotopic Molecular Weight376.204987621
IUPAC Name(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Namedesoximetasone
CAS Registry Number382-67-2
SMILES
[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI Identifier
InChI=1S/C22H29FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h6-7,9,12,15-16,18-19,24,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
InChI KeyVWVSBHGCDBMOOT-IIEHVVJPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • 20-oxosteroid
  • Pregnane-skeleton
  • 9-halo-steroid
  • Halo-steroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-hydroxy ketone
  • Cyclic alcohol
  • Ketone
  • Secondary alcohol
  • Halohydrin
  • Fluorohydrin
  • Cyclic ketone
  • Organic oxygen compound
  • Organohalogen compound
  • Organofluoride
  • Organooxygen compound
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point217 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.031 g/LNot Available
LogP2.3Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available186.45http://allccs.zhulab.cn/database/detail?ID=AllCCS00001212
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP10(2.13) g/LALOGPS
logP10(2.35) g/LChemAxon
logS10(-4.1) g/LALOGPS
pKa (Strongest Acidic)13.44ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity101.17 m³·mol⁻¹ChemAxon
Polarizability40.09 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Desoximetasone[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C3930.5Standard polar33892256
Desoximetasone[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C2793.7Standard non polar33892256
Desoximetasone[H][C@@]12C[C@@H](C)[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C3012.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Desoximetasone,1TMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C3285.2Semi standard non polar33892256
Desoximetasone,1TMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=O)CO3221.6Semi standard non polar33892256
Desoximetasone,1TMS,isomer #3C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)C1=C(CO)O[Si](C)(C)C3196.3Semi standard non polar33892256
Desoximetasone,1TMS,isomer #4C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C3211.6Semi standard non polar33892256
Desoximetasone,2TMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C3210.9Semi standard non polar33892256
Desoximetasone,2TMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C3193.5Semi standard non polar33892256
Desoximetasone,2TMS,isomer #3C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C3219.0Semi standard non polar33892256
Desoximetasone,2TMS,isomer #4C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO)O[Si](C)(C)C3129.5Semi standard non polar33892256
Desoximetasone,2TMS,isomer #5C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C3121.7Semi standard non polar33892256
Desoximetasone,3TMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C3109.9Semi standard non polar33892256
Desoximetasone,3TMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C3178.6Standard non polar33892256
Desoximetasone,3TMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C)O[Si](C)(C)C3381.2Standard polar33892256
Desoximetasone,3TMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C3151.8Semi standard non polar33892256
Desoximetasone,3TMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C3153.6Standard non polar33892256
Desoximetasone,3TMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C)O[Si](C)(C)C3416.6Standard polar33892256
Desoximetasone,1TBDMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C(C)(C)C3539.2Semi standard non polar33892256
Desoximetasone,1TBDMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=O)CO3442.2Semi standard non polar33892256
Desoximetasone,1TBDMS,isomer #3C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)C1=C(CO)O[Si](C)(C)C(C)(C)C3435.9Semi standard non polar33892256
Desoximetasone,1TBDMS,isomer #4C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C(C)(C)C3432.9Semi standard non polar33892256
Desoximetasone,2TBDMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=O)CO[Si](C)(C)C(C)(C)C3689.5Semi standard non polar33892256
Desoximetasone,2TBDMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3638.2Semi standard non polar33892256
Desoximetasone,2TBDMS,isomer #3C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3644.8Semi standard non polar33892256
Desoximetasone,2TBDMS,isomer #4C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO)O[Si](C)(C)C(C)(C)C3578.2Semi standard non polar33892256
Desoximetasone,2TBDMS,isomer #5C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO)O[Si](C)(C)C(C)(C)C3573.1Semi standard non polar33892256
Desoximetasone,3TBDMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3745.9Semi standard non polar33892256
Desoximetasone,3TBDMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3833.1Standard non polar33892256
Desoximetasone,3TBDMS,isomer #1C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)C1=C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3619.2Standard polar33892256
Desoximetasone,3TBDMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3785.0Semi standard non polar33892256
Desoximetasone,3TBDMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3805.8Standard non polar33892256
Desoximetasone,3TBDMS,isomer #2C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O[Si](C)(C)C(C)(C)C)C[C@]2(C)[C@H]1C(=CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3646.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Desoximetasone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05o0-0912000000-a19399cef0d27c3594e62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desoximetasone GC-MS (2 TMS) - 70eV, Positivesplash10-0a4i-2943160000-a934ab87ed20665cae692017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desoximetasone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Desoximetasone LC-ESI-qTof , Positive-QTOFsplash10-000i-0859000000-a10700f328db7dc715b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desoximetasone LC-ESI-qTof , Positive-QTOFsplash10-00di-2940000000-d3344c1ae6eb707917552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desoximetasone , positive-QTOFsplash10-000i-0859000000-a10700f328db7dc715b52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desoximetasone , positive-QTOFsplash10-00di-2940000000-d3344c1ae6eb707917552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desoximetasone 35V, Positive-QTOFsplash10-007a-0943000000-d694148b80e27bf503782021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Desoximetasone 35V, Negative-QTOFsplash10-056r-0097000000-b71d36aa7a284e10054e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 10V, Positive-QTOFsplash10-056r-0009000000-d0e87553c50e0a0145c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 20V, Positive-QTOFsplash10-0a6s-0109000000-07696481bbb48e48679f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 40V, Positive-QTOFsplash10-0kft-3498000000-c406362cf63dd705c6382016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 10V, Negative-QTOFsplash10-004i-0009000000-518050b225f1b7caa9122016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 20V, Negative-QTOFsplash10-0a6r-1009000000-bb5c7b442c44ba33b8cd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 40V, Negative-QTOFsplash10-0pba-4149000000-be3ea39b7602076596512016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 10V, Negative-QTOFsplash10-004i-0009000000-ae9873238f7091a31d622021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 20V, Negative-QTOFsplash10-014j-0009000000-ac020326894ee4a95c542021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 40V, Negative-QTOFsplash10-016s-0019000000-1ae4ef032615d49ca33a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 10V, Positive-QTOFsplash10-004i-0009000000-ccab12f64a156f1a55952021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 20V, Positive-QTOFsplash10-06fr-0329000000-c25e09b1c9425ea3a7fa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoximetasone 40V, Positive-QTOFsplash10-05g0-0794000000-aa7e0b33c97c418bc4792021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00547 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00547 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00547
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470604
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesoximetasone
METLIN IDNot Available
PubChem Compound5311067
PDB IDNot Available
ChEBI ID691037
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. 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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.