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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:12:11 UTC
Update Date2022-03-07 02:51:28 UTC
HMDB IDHMDB0013043
Secondary Accession Numbers
  • HMDB0013044
  • HMDB13043
  • HMDB13044
Metabolite Identification
Common NameProstaglandin PGE2 1-glyceryl ester
Description2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain,1 and has been characterized as the natural endocannabinoid ligand for the CB1 receptor.2 Incubation of 2-AG with COX-2 and specific prostaglandin H2 (PGH2) isomerases in cell cultures and isolated enzyme preparations results in prostaglandin glycerol ester formation.3 The biosynthesis of PGH, PGD, PGE, PGF, and TXA-2-glyceryl ester compounds have all been documented. The 2-glyceryl ester moiety equilibrates rapidly (within minutes) with the more stable 1-glyceryl ester, producing a 10:90 2:1-glyceryl ester mixture in typical aqueous media. While the stability and metabolism of these prostaglandin products has been investigated,4 little is known about their intrinsic biological activity.
Structure
Data?1582753086
Synonyms
ValueSource
1-(9,15-dioxo-11alpha-Hydroxy-(5Z,13E)-prostadienoyl)-glycerolHMDB
1-PGE(,2)-gHMDB
Prostaglandin pge(,2) 1-glycerolHMDB
(2R)-2,3-Dihydroxypropyl (5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acidGenerator
Chemical FormulaC23H38O7
Average Molecular Weight426.5436
Monoisotopic Molecular Weight426.26175357
IUPAC Name(2R)-2,3-dihydroxypropyl (5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoate
Traditional Name(2R)-2,3-dihydroxypropyl (5Z)-7-[(1R,2R,3S)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoate
CAS Registry NumberNot Available
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)OC[C@H](O)CO
InChI Identifier
InChI=1S/C23H38O7/c1-2-3-6-9-17(25)12-13-20-19(21(27)14-22(20)28)10-7-4-5-8-11-23(29)30-16-18(26)15-24/h4,7,12-13,17-20,22,24-26,28H,2-3,5-6,8-11,14-16H2,1H3/b7-4-,13-12+/t17-,18+,19+,20+,22-/m0/s1
InChI KeyRJXVYMMSQBYEHN-SDTVLRMPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Fatty alcohol
  • 1-acyl-sn-glycerol
  • Monoradylglycerol
  • Monoacylglycerol
  • Glycerolipid
  • Fatty acid ester
  • Cyclopentanol
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
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 Solubility0.15 g/LALOGPS
logP2.3ALOGPS
logP2.05ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.58ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity116.46 m³·mol⁻¹ChemAxon
Polarizability48.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+204.15631661259
DarkChem[M-H]-207.29931661259
DeepCCS[M+H]+203.1330932474
DeepCCS[M-H]-200.73430932474
DeepCCS[M-2H]-233.61730932474
DeepCCS[M+Na]+209.04230932474
AllCCS[M+H]+209.432859911
AllCCS[M+H-H2O]+207.332859911
AllCCS[M+NH4]+211.332859911
AllCCS[M+Na]+211.832859911
AllCCS[M-H]-204.932859911
AllCCS[M+Na-2H]-207.132859911
AllCCS[M+HCOO]-209.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Prostaglandin PGE2 1-glyceryl esterCCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)OC[C@H](O)CO4284.8Standard polar33892256
Prostaglandin PGE2 1-glyceryl esterCCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)OC[C@H](O)CO3097.0Standard non polar33892256
Prostaglandin PGE2 1-glyceryl esterCCCCC[C@H](O)\C=C\[C@H]1[C@@H](O)CC(=O)[C@@H]1C\C=C/CCCC(=O)OC[C@H](O)CO3423.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Prostaglandin PGE2 1-glyceryl ester,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C3300.9Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO3226.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TMS,isomer #3CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C3293.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C3288.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TMS,isomer #5CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C)C[C@@H]1O3251.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO3203.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C3170.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #10CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C3274.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #11CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O3256.4Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #12CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C3203.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #13CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O3250.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #14CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C3198.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)O[Si](C)(C)C3264.2Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)O[Si](C)(C)C3262.2Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #4CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C)C[C@@H]1O)O[Si](C)(C)C3252.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #5CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C3178.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C3214.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #7CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C3203.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #8CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3223.6Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TMS,isomer #9CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO3212.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)O[Si](C)(C)C3176.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #10CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C3198.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #11CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3215.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #12CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C3200.9Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #13CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3213.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #14CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C3199.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #15CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O3259.9Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #16CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C3219.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)O[Si](C)(C)C3179.9Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #3CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3182.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #4CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C3163.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #5CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3250.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #6CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O)O[Si](C)(C)C3258.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #7CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)O[Si](C)(C)C3188.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #8CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O)O[Si](C)(C)C3262.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TMS,isomer #9CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)O[Si](C)(C)C3191.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3196.4Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #2CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3215.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C)O[Si](C)(C)C3194.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #4CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3201.6Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #5CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C)O[Si](C)(C)C3181.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #6CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O)O[Si](C)(C)C3254.6Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #7CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3213.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #8CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C3226.2Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TMS,isomer #9CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C3215.6Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,5TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3247.4Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,5TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3197.7Standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,5TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3372.0Standard polar33892256
Prostaglandin PGE2 1-glyceryl ester,5TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3228.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,5TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2977.1Standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,5TMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3442.8Standard polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C(C)(C)C3533.6Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO3434.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C3519.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TBDMS,isomer #4CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C3528.9Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TBDMS,isomer #5CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O3509.4Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,1TBDMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO3428.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C(C)(C)C3652.6Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #10CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3742.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #11CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O3713.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #12CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C3648.6Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #13CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O3722.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #14CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C3662.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3742.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3746.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #4CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O)O[Si](C)(C)C(C)(C)C3734.4Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #5CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C(C)(C)C3653.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #6CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C3646.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #7CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C3651.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #8CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C3664.4Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,2TBDMS,isomer #9CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO3659.9Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3876.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #10CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3885.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #11CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C3880.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #12CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C3881.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #13CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C3887.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #14CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C3893.3Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #15CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O3948.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #16CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3897.2Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3891.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3893.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #4CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO)O[Si](C)(C)C(C)(C)C3884.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #5CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3986.8Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #6CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O)O[Si](C)(C)C(C)(C)C3956.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #7CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3889.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #8CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O)O[Si](C)(C)C(C)(C)C3970.2Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,3TBDMS,isomer #9CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3900.9Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4103.1Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4090.7Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #3CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4079.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #4CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4104.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #5CCCCC[C@@H](/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@H](O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4094.0Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #6CCCCC[C@@H](/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O)O[Si](C)(C)C(C)(C)C4167.2Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #7CCCCC[C@@H](/C=C/[C@H]1[C@@H](O)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4107.5Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #8CCCCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C4098.4Semi standard non polar33892256
Prostaglandin PGE2 1-glyceryl ester,4TBDMS,isomer #9CCCCC[C@H](O)/C=C/[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)[C@@H]1C/C=C\CCCC(=O)OC[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4097.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin PGE2 1-glyceryl ester GC-MS (3 TMS) - 70eV, Positivesplash10-056r-5255239000-e61e8401364415044dc52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin PGE2 1-glyceryl ester GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 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 - Prostaglandin PGE2 1-glyceryl ester 10V, Positive-QTOFsplash10-0006-0000900000-a7b6ab3f50632d2b03022017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 20V, Positive-QTOFsplash10-0006-0000900000-a7b6ab3f50632d2b03022017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 40V, Positive-QTOFsplash10-14n6-0006900000-af4723d1f81b0a505e3e2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 10V, Positive-QTOFsplash10-001i-0000900000-a4f46e2af85b363a3c4a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 20V, Positive-QTOFsplash10-001i-0000900000-a4f46e2af85b363a3c4a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 40V, Positive-QTOFsplash10-000t-9000500000-fd3e47eb539a531f630e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 10V, Positive-QTOFsplash10-0006-0000900000-5e14ba638d737caacdb62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 20V, Positive-QTOFsplash10-0006-0000900000-5e14ba638d737caacdb62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 40V, Positive-QTOFsplash10-0pe0-0008900000-f884254e9d2894c156362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 10V, Negative-QTOFsplash10-0540-4069400000-709c986128afec9e40132021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 20V, Negative-QTOFsplash10-0ac0-9027100000-bcfc47de24db916845552021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 40V, Negative-QTOFsplash10-0udj-1293000000-32873ab73b237edc1edf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 10V, Positive-QTOFsplash10-0006-0009200000-fb1ab0540ddfb828a0842021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 20V, Positive-QTOFsplash10-0006-2129100000-c928f6029feca70871fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Prostaglandin PGE2 1-glyceryl ester 40V, Positive-QTOFsplash10-014l-9811000000-be297e585132aab5d6332021-09-24Wishart 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 IDFDB029267
KNApSAcK IDNot Available
Chemspider ID30776691
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52193688
PDB IDNot Available
ChEBI ID165319
Food Biomarker OntologyNot Available
VMH IDCE5726
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.