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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002341
Secondary Accession Numbers
  • HMDB02341
Metabolite Identification
Common Name8-iso-15-keto-PGE2
Description8-iso-15-keto-PGE2 is an isoprostane. Isoprostanes are arachidonic acid metabolites produced by peroxidative attack of membrane lipids. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury. For this reason, they are frequently used as markers of oxidative stress; however, many are now finding that these molecules are not inert, but in fact evoke powerful biological responses in an increasing array of cell types. In many cases, these biological effects can account in part for the various features and manifestations of those clinical conditions. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states (PMID: 14504139 ). Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bone's mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, to induce uterine contractions and to activate platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1alpha and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID: 16978535 ). Prostaglandins 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?1582752244
Synonyms
ValueSource
(5Z,8b,11a,13E)-11-Hydroxy-9,15-dioxo-prosta-5,13-dien-1-OateHMDB
(5Z,8b,11a,13E)-11-Hydroxy-9,15-dioxo-prosta-5,13-dien-1-Oic acidHMDB
8-Iso-15-keto-prostaglandine e2HMDB
(5Z)-7-[(1S,2R)-3-Hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoateHMDB
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1S,2R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name8-iso-15-keto-PGE2
CAS Registry Number914804-63-0
SMILES
CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t16-,17+,19?/m0/s1
InChI KeyYRTJDWROBKPZNV-LSAJIUQUSA-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
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Unsaturated fatty acid
  • Fatty acid
  • Alpha,beta-unsaturated ketone
  • Cyclic alcohol
  • Acryloyl-group
  • Enone
  • Secondary alcohol
  • Cyclic ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.058 g/LALOGPS
logP3.27ALOGPS
logP3.64ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity98.54 m³·mol⁻¹ChemAxon
Polarizability39.99 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
DeepCCS[M+H]+201.58130932474
DeepCCS[M-H]-198.66930932474
DeepCCS[M-2H]-233.51430932474
DeepCCS[M+Na]+208.74230932474
AllCCS[M+H]+191.032859911
AllCCS[M+H-H2O]+188.332859911
AllCCS[M+NH4]+193.532859911
AllCCS[M+Na]+194.232859911
AllCCS[M-H]-190.632859911
AllCCS[M+Na-2H]-191.932859911
AllCCS[M+HCOO]-193.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-iso-15-keto-PGE2CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O4453.4Standard polar33892256
8-iso-15-keto-PGE2CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O2649.1Standard non polar33892256
8-iso-15-keto-PGE2CCCCCC(=O)\C=C\[C@H]1C(O)CC(=O)[C@H]1C\C=C/CCCC(O)=O2844.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-iso-15-keto-PGE2,1TMS,isomer #1CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O2774.4Semi standard non polar33892256
8-iso-15-keto-PGE2,1TMS,isomer #2CCCCCC(=O)/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2829.7Semi standard non polar33892256
8-iso-15-keto-PGE2,1TMS,isomer #3CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O2853.8Semi standard non polar33892256
8-iso-15-keto-PGE2,1TMS,isomer #4CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3110.9Semi standard non polar33892256
8-iso-15-keto-PGE2,1TMS,isomer #5CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O2761.1Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #1CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2704.6Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #2CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C2836.5Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #3CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3000.9Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #4CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O2755.4Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #5CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O2826.3Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #6CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3022.5Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #7CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2728.3Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #8CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C3090.5Semi standard non polar33892256
8-iso-15-keto-PGE2,2TMS,isomer #9CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3015.5Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C2782.9Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C2853.0Standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C2998.3Standard polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2964.9Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2887.2Standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3079.9Standard polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #3CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2749.4Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #3CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2792.7Standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #3CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C3062.3Standard polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C3054.9Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C2844.5Standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C3320.9Standard polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #5CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3008.4Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #5CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2771.7Standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #5CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3339.4Standard polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C3043.4Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C2882.3Standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O)O[Si](C)(C)C3381.7Standard polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #7CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2971.6Semi standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #7CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2818.2Standard non polar33892256
8-iso-15-keto-PGE2,3TMS,isomer #7CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3462.7Standard polar33892256
8-iso-15-keto-PGE2,4TMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C3012.2Semi standard non polar33892256
8-iso-15-keto-PGE2,4TMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C2905.9Standard non polar33892256
8-iso-15-keto-PGE2,4TMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)CC1O[Si](C)(C)C)O[Si](C)(C)C3016.4Standard polar33892256
8-iso-15-keto-PGE2,4TMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2984.1Semi standard non polar33892256
8-iso-15-keto-PGE2,4TMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2793.3Standard non polar33892256
8-iso-15-keto-PGE2,4TMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3070.5Standard polar33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #1CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O2997.2Semi standard non polar33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #2CCCCCC(=O)/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3089.1Semi standard non polar33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #3CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O3112.1Semi standard non polar33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #4CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3353.5Semi standard non polar33892256
8-iso-15-keto-PGE2,1TBDMS,isomer #5CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O3003.8Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #1CCCCCC(=O)/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3201.9Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #2CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C3286.0Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #3CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3460.1Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #4CCCCCC(=O)/C=C/[C@H]1C(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)O3247.6Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #5CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O3337.9Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #6CCCCC=C(/C=C/[C@H]1C(O)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3518.8Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #7CCCCCC(=O)/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3241.2Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #8CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C3569.7Semi standard non polar33892256
8-iso-15-keto-PGE2,2TBDMS,isomer #9CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3490.9Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C3483.2Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C3391.4Standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C3189.6Standard polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3664.7Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3434.1Standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1C(O[Si](C)(C)C(C)(C)C)CC(=O)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3253.6Standard polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #3CCCCCC(=O)/C=C/[C@H]1C(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)O[Si](C)(C)C(C)(C)C3454.4Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #3CCCCCC(=O)/C=C/[C@H]1C(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)O[Si](C)(C)C(C)(C)C3257.0Standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #3CCCCCC(=O)/C=C/[C@H]1C(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)O[Si](C)(C)C(C)(C)C3226.2Standard polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3723.9Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3348.2Standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3463.7Standard polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #5CCCCC=C(/C=C/[C@H]1C(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)O)O[Si](C)(C)C(C)(C)C3703.3Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #5CCCCC=C(/C=C/[C@H]1C(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)O)O[Si](C)(C)C(C)(C)C3169.1Standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #5CCCCC=C(/C=C/[C@H]1C(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)O)O[Si](C)(C)C(C)(C)C3491.4Standard polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C3761.8Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C3410.8Standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O)O[Si](C)(C)C(C)(C)C3502.5Standard polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #7CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3692.7Semi standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #7CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3240.7Standard non polar33892256
8-iso-15-keto-PGE2,3TBDMS,isomer #7CCCCC=C(/C=C/[C@H]1C(O)C=C(O[Si](C)(C)C(C)(C)C)[C@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3581.2Standard polar33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3896.0Semi standard non polar33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3543.8Standard non polar33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)CC1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3256.4Standard polar33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1C(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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3881.9Semi standard non polar33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1C(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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3315.9Standard non polar33892256
8-iso-15-keto-PGE2,4TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1C(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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3288.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-15-keto-PGE2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-4493000000-0d0c2247610da9ad51de2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-15-keto-PGE2 GC-MS (2 TMS) - 70eV, Positivesplash10-002b-7318900000-e3deca635536990d3ff82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-15-keto-PGE2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-iso-15-keto-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 - 8-iso-15-keto-PGE2 10V, Positive-QTOFsplash10-00lr-0029000000-9303b63bd2ebcbb5c3842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Positive-QTOFsplash10-067i-2195000000-4191e15aa7f06f807e382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Positive-QTOFsplash10-000i-9210000000-7c06db5bb5cf1359caab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 10V, Negative-QTOFsplash10-0002-0019000000-3ef3528ac5a012ba1cf72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Negative-QTOFsplash10-001j-3079000000-e1ebbca36295283f32e12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Negative-QTOFsplash10-0a4i-9452000000-aa26e5f3571b762113f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 10V, Negative-QTOFsplash10-001j-0019000000-319ec8417f062af25ae22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Negative-QTOFsplash10-008i-0094000000-ecf8159ba7722550f80a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Negative-QTOFsplash10-053u-9270000000-4f5b9ab71a4cd04afdc92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 10V, Positive-QTOFsplash10-0159-0019000000-e747c20277d6c7786fa32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 20V, Positive-QTOFsplash10-014i-6369000000-c74c0a7bb044927841f92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-iso-15-keto-PGE2 40V, Positive-QTOFsplash10-00kf-9200000000-e6002eb037e36f06c2422021-09-25Wishart 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 IDFDB022970
KNApSAcK IDNot Available
Chemspider ID35013045
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477750
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. Tazzeo T, Miller J, Janssen LJ: Vasoconstrictor responses, and underlying mechanisms, to isoprostanes in human and porcine bronchial arterial smooth muscle. Br J Pharmacol. 2003 Oct;140(4):759-63. Epub 2003 Sep 22. [PubMed:14504139 ]
  2. Harizi H, Gualde N: Pivotal role of PGE2 and IL-10 in the cross-regulation of dendritic cell-derived inflammatory mediators. Cell Mol Immunol. 2006 Aug;3(4):271-7. [PubMed:16978535 ]