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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-05-01 17:30:28 UTC
Update Date2021-09-14 15:46:21 UTC
HMDB IDHMDB0060054
Secondary Accession Numbers
  • HMDB60054
Metabolite Identification
Common Namebicyclo-PGE2
Descriptionbicyclo Prostaglandin E2 (bicyclo-PGE2) is a stable breakdown product of PGE2 and 13,14-dihydro-15-keto PGE2. Bicyclo PGE2 is a stable, base-catalyzed transformation product of 13,14-dihydro-15-keto PGE2. 13,14-dihydro-15-keto PGE2 itself is a metabolite of PGE2 found in human plasma at a median level of 20-25 pg/ml. Due to the inherent instability of 13,14-dihydro-15-keto PGE2, it is advisable to quantify it as bicyclo PGE2 to estimate PGE2 biosynthesis or metabolism in vivo. (http://bioreagent.bertinpharma.com/)
Structure
Data?1563866010
SynonymsNot Available
Chemical FormulaC20H30O4
Average Molecular Weight334.4498
Monoisotopic Molecular Weight334.214409448
IUPAC Name(5Z)-7-[(1R,3aS,7aS)-4-butyl-2,5-dioxo-octahydro-1H-inden-1-yl]hept-5-enoic acid
Traditional Namebicyclo-PGE2
CAS Registry NumberNot Available
SMILES
CCCCC1[C@H]2CC(=O)[C@H](C\C=C/CCCC(O)=O)[C@H]2CCC1=O
InChI Identifier
InChI=1S/C20H30O4/c1-2-3-8-16-17-13-19(22)15(14(17)11-12-18(16)21)9-6-4-5-7-10-20(23)24/h4,6,14-17H,2-3,5,7-13H2,1H3,(H,23,24)/b6-4-/t14-,15-,16?,17+/m1/s1
InChI KeyCGCZPIJMGKLVTQ-PAJBVNRRSA-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
  • Medium-chain fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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 Solubility0.029 g/LALOGPS
logP4.18ALOGPS
logP4.27ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity94.12 m³·mol⁻¹ChemAxon
Polarizability38.69 ųChemAxon
Number of Rings2ChemAxon
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]+181.42331661259
DarkChem[M-H]-180.10731661259
DeepCCS[M+H]+193.63930932474
DeepCCS[M-H]-190.71430932474
DeepCCS[M-2H]-225.57330932474
DeepCCS[M+Na]+201.6530932474
AllCCS[M+H]+186.032859911
AllCCS[M+H-H2O]+183.232859911
AllCCS[M+NH4]+188.632859911
AllCCS[M+Na]+189.332859911
AllCCS[M-H]-189.132859911
AllCCS[M+Na-2H]-190.032859911
AllCCS[M+HCOO]-191.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
bicyclo-PGE2CCCCC1[C@H]2CC(=O)[C@H](C\C=C/CCCC(O)=O)[C@H]2CCC1=O4064.3Standard polar33892256
bicyclo-PGE2CCCCC1[C@H]2CC(=O)[C@H](C\C=C/CCCC(O)=O)[C@H]2CCC1=O2709.7Standard non polar33892256
bicyclo-PGE2CCCCC1[C@H]2CC(=O)[C@H](C\C=C/CCCC(O)=O)[C@H]2CCC1=O2631.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
bicyclo-PGE2,1TMS,isomer #1CCCCC1C(=O)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2763.2Semi standard non polar33892256
bicyclo-PGE2,1TMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]122793.9Semi standard non polar33892256
bicyclo-PGE2,1TMS,isomer #3CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O2747.0Semi standard non polar33892256
bicyclo-PGE2,1TMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O)C(O[Si](C)(C)C)=C[C@H]122748.4Semi standard non polar33892256
bicyclo-PGE2,1TMS,isomer #5CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O2752.3Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #1CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2704.5Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #1CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2838.0Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #1CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C3130.8Standard polar33892256
bicyclo-PGE2,2TMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]122745.8Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]122807.7Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]123158.4Standard polar33892256
bicyclo-PGE2,2TMS,isomer #3CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2712.3Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #3CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2753.0Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #3CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C3160.5Standard polar33892256
bicyclo-PGE2,2TMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C[C@H]122694.2Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C[C@H]122808.2Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(O[Si](C)(C)C)=C[C@H]123221.2Standard polar33892256
bicyclo-PGE2,2TMS,isomer #5CCCCC1=C(O[Si](C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]122760.3Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #5CCCCC1=C(O[Si](C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]122786.9Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #5CCCCC1=C(O[Si](C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]123320.2Standard polar33892256
bicyclo-PGE2,2TMS,isomer #6CCCCC1C(O[Si](C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]122741.6Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #6CCCCC1C(O[Si](C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]122735.4Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #6CCCCC1C(O[Si](C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]123348.1Standard polar33892256
bicyclo-PGE2,2TMS,isomer #7CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O2677.5Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #7CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O2793.0Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #7CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O3368.4Standard polar33892256
bicyclo-PGE2,2TMS,isomer #8CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O2684.8Semi standard non polar33892256
bicyclo-PGE2,2TMS,isomer #8CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O2738.9Standard non polar33892256
bicyclo-PGE2,2TMS,isomer #8CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O3379.2Standard polar33892256
bicyclo-PGE2,3TMS,isomer #1CCCCC1=C(O[Si](C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]122727.5Semi standard non polar33892256
bicyclo-PGE2,3TMS,isomer #1CCCCC1=C(O[Si](C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]122880.5Standard non polar33892256
bicyclo-PGE2,3TMS,isomer #1CCCCC1=C(O[Si](C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]123000.6Standard polar33892256
bicyclo-PGE2,3TMS,isomer #2CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2676.6Semi standard non polar33892256
bicyclo-PGE2,3TMS,isomer #2CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2869.6Standard non polar33892256
bicyclo-PGE2,3TMS,isomer #2CCCCC1=C(O[Si](C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C3074.9Standard polar33892256
bicyclo-PGE2,3TMS,isomer #3CCCCC1C(O[Si](C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]122740.8Semi standard non polar33892256
bicyclo-PGE2,3TMS,isomer #3CCCCC1C(O[Si](C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]122816.9Standard non polar33892256
bicyclo-PGE2,3TMS,isomer #3CCCCC1C(O[Si](C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]123032.0Standard polar33892256
bicyclo-PGE2,3TMS,isomer #4CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2700.9Semi standard non polar33892256
bicyclo-PGE2,3TMS,isomer #4CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C2799.4Standard non polar33892256
bicyclo-PGE2,3TMS,isomer #4CCCCC1C(O[Si](C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C3083.9Standard polar33892256
bicyclo-PGE2,1TBDMS,isomer #1CCCCC1C(=O)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3037.0Semi standard non polar33892256
bicyclo-PGE2,1TBDMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123052.3Semi standard non polar33892256
bicyclo-PGE2,1TBDMS,isomer #3CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O2980.0Semi standard non polar33892256
bicyclo-PGE2,1TBDMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O)C(O[Si](C)(C)C(C)(C)C)=C[C@H]122980.2Semi standard non polar33892256
bicyclo-PGE2,1TBDMS,isomer #5CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O3004.8Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #1CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3203.6Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #1CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3228.5Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #1CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3292.8Standard polar33892256
bicyclo-PGE2,2TBDMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123269.0Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123222.0Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #2CCCCC1C(=O)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123304.3Standard polar33892256
bicyclo-PGE2,2TBDMS,isomer #3CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3221.0Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #3CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3058.9Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #3CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1CC(=O)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3287.3Standard polar33892256
bicyclo-PGE2,2TBDMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C[C@H]123179.3Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C[C@H]123117.3Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #4CCCCC1C(=O)CC[C@@H]2[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C[C@H]123333.1Standard polar33892256
bicyclo-PGE2,2TBDMS,isomer #5CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123213.8Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #5CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123140.4Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #5CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123453.8Standard polar33892256
bicyclo-PGE2,2TBDMS,isomer #6CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123221.0Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #6CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123002.0Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #6CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123462.6Standard polar33892256
bicyclo-PGE2,2TBDMS,isomer #7CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O3117.3Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #7CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O3059.6Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #7CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O3485.3Standard polar33892256
bicyclo-PGE2,2TBDMS,isomer #8CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O3146.7Semi standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #8CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O2950.1Standard non polar33892256
bicyclo-PGE2,2TBDMS,isomer #8CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O3482.0Standard polar33892256
bicyclo-PGE2,3TBDMS,isomer #1CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123425.2Semi standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #1CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123379.4Standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #1CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123243.1Standard polar33892256
bicyclo-PGE2,3TBDMS,isomer #2CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3335.6Semi standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #2CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3253.1Standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #2CCCCC1=C(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3268.8Standard polar33892256
bicyclo-PGE2,3TBDMS,isomer #3CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123453.8Semi standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #3CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123214.0Standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #3CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]2C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C[C@H]123231.2Standard polar33892256
bicyclo-PGE2,3TBDMS,isomer #4CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3387.0Semi standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #4CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3142.0Standard non polar33892256
bicyclo-PGE2,3TBDMS,isomer #4CCCCC1C(O[Si](C)(C)C(C)(C)C)=CC[C@H]2[C@@H]1C=C(O[Si](C)(C)C(C)(C)C)[C@@H]2C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3251.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - bicyclo-PGE2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-2392000000-430ba221c45d5fafc62a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - bicyclo-PGE2 GC-MS (1 TMS) - 70eV, Positivesplash10-03kc-6449000000-3a3e981f4f5fc8a330302017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - bicyclo-PGE2 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 - bicyclo-PGE2 10V, Positive-QTOFsplash10-014r-0059000000-5b89af0a6089b2daa8dd2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 20V, Positive-QTOFsplash10-014r-4293000000-9cc24dae909f9379c3762017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 40V, Positive-QTOFsplash10-01bl-9030000000-60014eac3066b05206732017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 10V, Negative-QTOFsplash10-001i-0019000000-479e0aafc7ea24f0062e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 20V, Negative-QTOFsplash10-00m0-1049000000-489bba9dc551c7c41f032017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 40V, Negative-QTOFsplash10-0a4i-9261000000-e29db6fede40d8a03c6d2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 10V, Positive-QTOFsplash10-00kb-0095000000-823cc55e055709107a0d2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 20V, Positive-QTOFsplash10-00mk-1193000000-240e2d625ce2f46c62872021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 40V, Positive-QTOFsplash10-00lu-9500000000-47ccf3ac55ba939078f52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 10V, Negative-QTOFsplash10-001i-0009000000-dee29a4ccbc66c032d502021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 20V, Negative-QTOFsplash10-001i-0029000000-cc2a67846ca552b3fc3f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - bicyclo-PGE2 40V, Negative-QTOFsplash10-000l-2492000000-96a4b066a987491a39872021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000039 +/- 0.000002 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283043
PDB IDNot Available
ChEBI ID89568
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. Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.