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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:38 UTC
Update Date2022-03-07 02:49:18 UTC
HMDB IDHMDB0003175
Secondary Accession Numbers
  • HMDB03175
Metabolite Identification
Common Name15-Keto-prostaglandin E2
Description15-keto-PGE2 is one of the prostaglandin E2 metabolites. (PMID 7190512 ). It is a degradation product produced by 15-hydroxy prostaglandin dehydrogenase (PGDH or 15-PGDH). 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?1582752265
Synonyms
ValueSource
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoateChEBI
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoateChEBI
15-Deoxy-15-oxo-prostaglandin e2ChEBI
15-Keto-pge2ChEBI
15-Ketoprostaglandin e2ChEBI
15-oxo-PGE2ChEBI
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoateGenerator
(5Z)-(15S)-11a-Hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z)-(15S)-11alpha-Hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoateGenerator
(5Z)-(15S)-11Α-hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
(5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoateGenerator
(5Z,13E)-11a-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z,13E)-11alpha-Hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoateGenerator
(5Z,13E)-11Α-hydroxy-9,15-dioxoprost-13-enoic acidGenerator
(5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoateHMDB
(5Z)-(13E)-11-alpha-Hydroxy-9,15-dioxoprosta-5,13-dienoic acidHMDB
(5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoateHMDB
(5Z,13E)-11-alpha-Hydroxy-9,15-dioxoprost-5,13-dienoic acidHMDB
15-Keto-pge2-alphaHMDB
15-oxo-PGE2-alphaHMDB
9,15-Dioxo-11-hydroxyprosta-5,13-dienoic acidHMDB
15-Ketoprostaglandin e2, (11alpha)-isomerHMDB
15-Keto-prostaglandin e2ChEBI
Chemical FormulaC20H30O5
Average Molecular Weight350.4492
Monoisotopic Molecular Weight350.20932407
IUPAC Name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
Traditional Name15-Keto-PGE2
CAS Registry Number26441-05-4
SMILES
CCCCCC(=O)\C=C\[C@H]1[C@H](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-/m1/s1
InChI KeyYRTJDWROBKPZNV-KMXMBPPJSA-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 Descriptors
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
Polarizability40.05 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]+199.81330932474
DeepCCS[M-H]-197.45530932474
DeepCCS[M-2H]-231.5230932474
DeepCCS[M+Na]+206.72430932474
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
15-Keto-prostaglandin E2CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O4462.3Standard polar33892256
15-Keto-prostaglandin E2CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O2610.6Standard non polar33892256
15-Keto-prostaglandin E2CCCCCC(=O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O2860.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
15-Keto-prostaglandin E2,1TMS,isomer #1CCCCCC(=O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O2730.3Semi standard non polar33892256
15-Keto-prostaglandin E2,1TMS,isomer #2CCCCCC(=O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2794.8Semi standard non polar33892256
15-Keto-prostaglandin E2,1TMS,isomer #3CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O2820.3Semi standard non polar33892256
15-Keto-prostaglandin E2,1TMS,isomer #4CCCCC=C(/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3091.5Semi standard non polar33892256
15-Keto-prostaglandin E2,1TMS,isomer #5CCCCCC(=O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O2721.8Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #1CCCCCC(=O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2683.8Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #2CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C2800.6Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #3CCCCC=C(/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2989.6Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #4CCCCCC(=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)O2740.6Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #5CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O2812.0Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #6CCCCC=C(/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3009.5Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #7CCCCCC(=O)/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2713.8Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #8CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C3067.5Semi standard non polar33892256
15-Keto-prostaglandin E2,2TMS,isomer #9CCCCC=C(/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C2990.4Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C2777.7Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C2847.5Standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #1CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C2939.5Standard polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #2CCCCC=C(/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2955.9Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #2CCCCC=C(/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2852.7Standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #2CCCCC=C(/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3055.3Standard polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #3CCCCCC(=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)O[Si](C)(C)C2735.2Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #3CCCCCC(=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)O[Si](C)(C)C2770.1Standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #3CCCCCC(=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)O[Si](C)(C)C3008.5Standard polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C3037.5Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C2841.7Standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C3317.8Standard polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #5CCCCC=C(/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)O)O[Si](C)(C)C2996.5Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #5CCCCC=C(/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)O)O[Si](C)(C)C2752.3Standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #5CCCCC=C(/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)O)O[Si](C)(C)C3333.5Standard polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C3030.0Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C2880.7Standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #6CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O)O[Si](C)(C)C3382.0Standard polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #7CCCCC=C(/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2963.1Semi standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #7CCCCC=C(/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2800.0Standard non polar33892256
15-Keto-prostaglandin E2,3TMS,isomer #7CCCCC=C(/C=C/[C@H]1[C@H](O)C=C(O[Si](C)(C)C)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C3459.0Standard polar33892256
15-Keto-prostaglandin E2,4TMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C3004.6Semi standard non polar33892256
15-Keto-prostaglandin E2,4TMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C2904.3Standard non polar33892256
15-Keto-prostaglandin E2,4TMS,isomer #1CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(O[Si](C)(C)C)C[C@H]1O[Si](C)(C)C)O[Si](C)(C)C3000.5Standard polar33892256
15-Keto-prostaglandin E2,4TMS,isomer #2CCCCC=C(/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)O[Si](C)(C)C)O[Si](C)(C)C2976.3Semi standard non polar33892256
15-Keto-prostaglandin E2,4TMS,isomer #2CCCCC=C(/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)O[Si](C)(C)C)O[Si](C)(C)C2772.8Standard non polar33892256
15-Keto-prostaglandin E2,4TMS,isomer #2CCCCC=C(/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)O[Si](C)(C)C)O[Si](C)(C)C3050.7Standard polar33892256
15-Keto-prostaglandin E2,1TBDMS,isomer #1CCCCCC(=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)O2955.8Semi standard non polar33892256
15-Keto-prostaglandin E2,1TBDMS,isomer #2CCCCCC(=O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3052.7Semi standard non polar33892256
15-Keto-prostaglandin E2,1TBDMS,isomer #3CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O3064.9Semi standard non polar33892256
15-Keto-prostaglandin E2,1TBDMS,isomer #4CCCCC=C(/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3333.5Semi standard non polar33892256
15-Keto-prostaglandin E2,1TBDMS,isomer #5CCCCCC(=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)O2959.8Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #1CCCCCC(=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)O[Si](C)(C)C(C)(C)C3175.9Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #2CCCCCC(=O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O[Si](C)(C)C(C)(C)C3244.3Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #3CCCCC=C(/C=C/[C@H]1[C@H](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)C3438.3Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #4CCCCCC(=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)O3214.6Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,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)C[C@H]1O3295.7Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #6CCCCC=C(/C=C/[C@H]1[C@H](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)C3499.6Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #7CCCCCC(=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)O[Si](C)(C)C(C)(C)C3212.3Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #8CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O)O[Si](C)(C)C(C)(C)C3532.0Semi standard non polar33892256
15-Keto-prostaglandin E2,2TBDMS,isomer #9CCCCC=C(/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)O)O[Si](C)(C)C(C)(C)C3457.8Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,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)C[C@H]1O[Si](C)(C)C(C)(C)C3442.3Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,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)C[C@H]1O[Si](C)(C)C(C)(C)C3368.5Standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,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)C[C@H]1O[Si](C)(C)C(C)(C)C3155.2Standard polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1[C@H](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)C3649.6Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1[C@H](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)C3377.8Standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #2CCCCC=C(/C=C/[C@H]1[C@H](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)C3237.5Standard polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #3CCCCCC(=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)O[Si](C)(C)C(C)(C)C3431.8Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #3CCCCCC(=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)O[Si](C)(C)C(C)(C)C3201.1Standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #3CCCCCC(=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)O[Si](C)(C)C(C)(C)C3189.2Standard polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=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)C3679.7Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=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)C3330.2Standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #4CCCCC=C(/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=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)C3459.3Standard polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #5CCCCC=C(/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)O)O[Si](C)(C)C(C)(C)C3669.8Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #5CCCCC=C(/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)O)O[Si](C)(C)C(C)(C)C3119.3Standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #5CCCCC=C(/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)O)O[Si](C)(C)C(C)(C)C3482.6Standard polar33892256
15-Keto-prostaglandin E2,3TBDMS,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)C[C@H]1O)O[Si](C)(C)C(C)(C)C3737.1Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,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)C[C@H]1O)O[Si](C)(C)C(C)(C)C3392.8Standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,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)C[C@H]1O)O[Si](C)(C)C(C)(C)C3503.7Standard polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #7CCCCC=C(/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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3683.0Semi standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #7CCCCC=C(/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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3186.2Standard non polar33892256
15-Keto-prostaglandin E2,3TBDMS,isomer #7CCCCC=C(/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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3578.1Standard polar33892256
15-Keto-prostaglandin E2,4TBDMS,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)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3856.7Semi standard non polar33892256
15-Keto-prostaglandin E2,4TBDMS,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)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3518.3Standard non polar33892256
15-Keto-prostaglandin E2,4TBDMS,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)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3248.4Standard polar33892256
15-Keto-prostaglandin E2,4TBDMS,isomer #2CCCCC=C(/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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3863.7Semi standard non polar33892256
15-Keto-prostaglandin E2,4TBDMS,isomer #2CCCCC=C(/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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3261.7Standard non polar33892256
15-Keto-prostaglandin E2,4TBDMS,isomer #2CCCCC=C(/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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3273.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15-Keto-prostaglandin E2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-052u-4493000000-0d0c2247610da9ad51de2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Keto-prostaglandin E2 GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-4101900000-afa0e89ef36aaefae13a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Keto-prostaglandin E2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Keto-prostaglandin E2 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 - 15-Keto-prostaglandin E2 10V, Positive-QTOFsplash10-00lr-0029000000-9303b63bd2ebcbb5c3842017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 20V, Positive-QTOFsplash10-067i-2195000000-4191e15aa7f06f807e382017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 40V, Positive-QTOFsplash10-000i-9210000000-7c06db5bb5cf1359caab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 10V, Negative-QTOFsplash10-0002-0019000000-3ef3528ac5a012ba1cf72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 20V, Negative-QTOFsplash10-001j-3079000000-e1ebbca36295283f32e12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 40V, Negative-QTOFsplash10-0a4i-9452000000-aa26e5f3571b762113f32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 10V, Negative-QTOFsplash10-001j-0019000000-319ec8417f062af25ae22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 20V, Negative-QTOFsplash10-008i-0094000000-ecf8159ba7722550f80a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 40V, Negative-QTOFsplash10-053u-9270000000-4f5b9ab71a4cd04afdc92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 10V, Positive-QTOFsplash10-0159-0019000000-e747c20277d6c7786fa32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 20V, Positive-QTOFsplash10-014i-6369000000-c74c0a7bb044927841f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Keto-prostaglandin E2 40V, Positive-QTOFsplash10-00kf-9200000000-e6002eb037e36f06c2422021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0006 (0.0002 - 0.0078) uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023119
KNApSAcK IDNot Available
Chemspider ID4444303
KEGG Compound IDC04707
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID2309
PubChem Compound5280719
PDB IDNot Available
ChEBI ID15547
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. Fitzpatrick FA, Liggett WF, Wynalda MA: Albumin-eicosanoid interactions. A model system to determine their attributes and inhibition. J Biol Chem. 1984 Mar 10;259(5):2722-7. [PubMed:6698991 ]
  2. Yang P, Felix E, Madden T, Fischer SM, Newman RA: Quantitative high-performance liquid chromatography/electrospray ionization tandem mass spectrometric analysis of 2- and 3-series prostaglandins in cultured tumor cells. Anal Biochem. 2002 Sep 1;308(1):168-77. [PubMed:12234478 ]
  3. 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 ]
  4. Gordon-Wright AP, Elder MG: Effect of prostaglandin E2 and its metabolites on lower segment myometrium in vitro. Eur J Obstet Gynecol Reprod Biol. 1980 Jun;10(5):297-302. [PubMed:7190512 ]