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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-04 15:06:09 UTC
Update Date2022-09-22 18:34:16 UTC
HMDB IDHMDB0001908
Secondary Accession Numbers
  • HMDB01908
Metabolite Identification
Common Name19-Hydroxy-PGE2
Description19-Hydroxy-PGE2 is a derivative of PGE2. Both 19-Hydroxy-PGE1 and 19-hydroxy-PGE2 are formed from PGE1 and PGE2 by prostaglandin 19-hydroxylase, a cytochrome P-450 enzyme, in seminal vesicles (PMID: 3196735 ). 19-Hydroxy-PGE2 is a selective prostanoid EP2-receptor agonist; it doesn't stimulate FP-receptors, and is devoid of activity on thromboxane A2, prostaglandin D2 and prostacyclin sensitive receptors. 19-OH PGE2 is formed in large quantities from PGE2 in human seminal plasma. PGE2 is 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). (PMID: 16978535 , 8248550 , 817207 ). 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?1582752216
Synonyms
ValueSource
19(R)-Hydroxy-pge2HMDB
19(R)-Hydroxy-prostaglandin e2HMDB
19R-19-Hydroxy pge-2HMDB
9-oxo-11R,15S,19R-Trihydroxy-5Z,13E-prostadienoateHMDB
9-oxo-11R,15S,19R-Trihydroxy-5Z,13E-prostadienoic acidHMDB
EganoprostHMDB
19-Hydroxyprostaglandin e2HMDB
19-Hydroxy-pge2MeSH
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
IUPAC Name(5Z)-7-[(1R,2R,3R)-2-[(1E,3S,7R)-3,7-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid
Traditional Name19-hydroxy-PGE2
CAS Registry Number55123-68-7
SMILES
C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O6/c1-14(21)7-6-8-15(22)11-12-17-16(18(23)13-19(17)24)9-4-2-3-5-10-20(25)26/h2,4,11-12,14-17,19,21-22,24H,3,5-10,13H2,1H3,(H,25,26)/b4-2-,12-11+/t14-,15+,16-,17-,19-/m1/s1
InChI KeyWTJYDBMHYPQFNJ-ZUVVJKHESA-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
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • 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 Solubility0.23 g/LALOGPS
logP1.99ALOGPS
logP1.76ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity101.18 m³·mol⁻¹ChemAxon
Polarizability41.84 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]+188.52931661259
DarkChem[M-H]-187.71431661259
AllCCS[M+H]+195.47132859911
AllCCS[M-H]-193.232859911
DeepCCS[M+H]+206.99330932474
DeepCCS[M-H]-204.59730932474
DeepCCS[M-2H]-237.68630932474
DeepCCS[M+Na]+213.09130932474
AllCCS[M+H]+195.532859911
AllCCS[M+H-H2O]+192.932859911
AllCCS[M+NH4]+197.832859911
AllCCS[M+Na]+198.532859911
AllCCS[M-H]-193.232859911
AllCCS[M+Na-2H]-194.632859911
AllCCS[M+HCOO]-196.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
19-Hydroxy-PGE2C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O4685.2Standard polar33892256
19-Hydroxy-PGE2C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O2827.1Standard non polar33892256
19-Hydroxy-PGE2C[C@@H](O)CCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O3090.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
19-Hydroxy-PGE2,1TMS,isomer #1C[C@H](CCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3064.5Semi standard non polar33892256
19-Hydroxy-PGE2,1TMS,isomer #2C[C@@H](O)CCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C3041.0Semi standard non polar33892256
19-Hydroxy-PGE2,1TMS,isomer #3C[C@@H](O)CCC[C@H](O)/C=C/[C@H]1[C@H](O[Si](C)(C)C)CC(=O)[C@@H]1C/C=C\CCCC(=O)O2953.6Semi standard non polar33892256
19-Hydroxy-PGE2,1TMS,isomer #4C[C@@H](O)CCC[C@H](O)/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O[Si](C)(C)C2999.5Semi standard non polar33892256
19-Hydroxy-PGE2,1TMS,isomer #5C[C@@H](O)CCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C)C[C@H]1O2950.9Semi standard non polar33892256
19-Hydroxy-PGE2,1TMS,isomer #6C[C@@H](O)CCC[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)O2901.8Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #1C[C@H](CCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O[Si](C)(C)C)O[Si](C)(C)C3024.5Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #10C[C@@H](O)CCC[C@H](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)C2905.6Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #11C[C@@H](O)CCC[C@H](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)C2951.2Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #12C[C@@H](O)CCC[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)O2925.8Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #13C[C@@H](O)CCC[C@H](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]1O2962.9Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #14C[C@@H](O)CCC[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)O[Si](C)(C)C2898.7Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #2C[C@H](CCC[C@H](O)/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)C2931.5Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #3C[C@H](CCC[C@H](O)/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)C2976.6Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #4C[C@H](CCC[C@H](O)/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)C2987.8Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #5C[C@H](CCC[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)O)O[Si](C)(C)C2907.6Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #6C[C@@H](O)CCC[C@@H](/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)C2912.0Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #7C[C@@H](O)CCC[C@@H](/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)C2965.5Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #8C[C@@H](O)CCC[C@@H](/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)C2990.3Semi standard non polar33892256
19-Hydroxy-PGE2,2TMS,isomer #9C[C@@H](O)CCC[C@@H](/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)C2890.6Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #1C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2890.9Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #10C[C@@H](O)CCC[C@@H](/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)C2849.9Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #11C[C@@H](O)CCC[C@@H](/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)C2930.7Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #12C[C@@H](O)CCC[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)O)O[Si](C)(C)C2895.9Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #13C[C@@H](O)CCC[C@@H](/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)C2939.2Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #14C[C@@H](O)CCC[C@@H](/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)C2869.6Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #15C[C@@H](O)CCC[C@H](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)C2931.3Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #16C[C@@H](O)CCC[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)O[Si](C)(C)C2885.4Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #2C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2952.3Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #3C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2987.3Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #4C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2909.8Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #5C[C@H](CCC[C@H](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)C)O[Si](C)(C)C2885.5Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #6C[C@H](CCC[C@H](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)C)O[Si](C)(C)C2960.4Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #7C[C@H](CCC[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)O)O[Si](C)(C)C2917.5Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #8C[C@H](CCC[C@H](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)O[Si](C)(C)C2954.5Semi standard non polar33892256
19-Hydroxy-PGE2,3TMS,isomer #9C[C@H](CCC[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)O[Si](C)(C)C)O[Si](C)(C)C2892.5Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #1C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2895.0Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #2C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2948.6Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #3C[C@H](CCC[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)O)O[Si](C)(C)C)O[Si](C)(C)C2920.2Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #4C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2966.2Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #5C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2915.8Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #6C[C@H](CCC[C@H](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)C)O[Si](C)(C)C2929.4Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #7C[C@H](CCC[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)O[Si](C)(C)C)O[Si](C)(C)C2908.2Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #8C[C@@H](O)CCC[C@@H](/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)C2909.0Semi standard non polar33892256
19-Hydroxy-PGE2,4TMS,isomer #9C[C@@H](O)CCC[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)O[Si](C)(C)C)O[Si](C)(C)C2887.4Semi standard non polar33892256
19-Hydroxy-PGE2,5TMS,isomer #1C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2955.4Semi standard non polar33892256
19-Hydroxy-PGE2,5TMS,isomer #1C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C3020.6Standard non polar33892256
19-Hydroxy-PGE2,5TMS,isomer #1C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C2981.8Standard polar33892256
19-Hydroxy-PGE2,5TMS,isomer #2C[C@H](CCC[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)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2946.5Semi standard non polar33892256
19-Hydroxy-PGE2,5TMS,isomer #2C[C@H](CCC[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)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2839.7Standard non polar33892256
19-Hydroxy-PGE2,5TMS,isomer #2C[C@H](CCC[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)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3050.7Standard polar33892256
19-Hydroxy-PGE2,1TBDMS,isomer #1C[C@H](CCC[C@H](O)/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)C3293.0Semi standard non polar33892256
19-Hydroxy-PGE2,1TBDMS,isomer #2C[C@@H](O)CCC[C@@H](/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)C3280.8Semi standard non polar33892256
19-Hydroxy-PGE2,1TBDMS,isomer #3C[C@@H](O)CCC[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)O3164.9Semi standard non polar33892256
19-Hydroxy-PGE2,1TBDMS,isomer #4C[C@@H](O)CCC[C@H](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)C3256.8Semi standard non polar33892256
19-Hydroxy-PGE2,1TBDMS,isomer #5C[C@@H](O)CCC[C@H](O)/C=C/[C@@H]1C(C/C=C\CCCC(=O)O)=C(O[Si](C)(C)C(C)(C)C)C[C@H]1O3240.8Semi standard non polar33892256
19-Hydroxy-PGE2,1TBDMS,isomer #6C[C@@H](O)CCC[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)O3138.6Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #1C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C(C)(C)C3533.7Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #10C[C@@H](O)CCC[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)O[Si](C)(C)C(C)(C)C3370.1Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #11C[C@@H](O)CCC[C@H](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)C3392.3Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #12C[C@@H](O)CCC[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)O3366.9Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #13C[C@@H](O)CCC[C@H](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]1O3442.8Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #14C[C@@H](O)CCC[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)O[Si](C)(C)C(C)(C)C3366.2Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #2C[C@H](CCC[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)O)O[Si](C)(C)C(C)(C)C3368.4Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #3C[C@H](CCC[C@H](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)C)O[Si](C)(C)C(C)(C)C3475.8Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #4C[C@H](CCC[C@H](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)O[Si](C)(C)C(C)(C)C3458.2Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #5C[C@H](CCC[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)O)O[Si](C)(C)C(C)(C)C3356.0Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #6C[C@@H](O)CCC[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)O)O[Si](C)(C)C(C)(C)C3370.1Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #7C[C@@H](O)CCC[C@@H](/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)C3463.7Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #8C[C@@H](O)CCC[C@@H](/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)C3451.2Semi standard non polar33892256
19-Hydroxy-PGE2,2TBDMS,isomer #9C[C@@H](O)CCC[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)O)O[Si](C)(C)C(C)(C)C3353.3Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #1C[C@H](CCC[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)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3616.4Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #10C[C@@H](O)CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3572.5Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #11C[C@@H](O)CCC[C@@H](/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)C3586.6Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #12C[C@@H](O)CCC[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)O)O[Si](C)(C)C(C)(C)C3576.3Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #13C[C@@H](O)CCC[C@@H](/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)C3647.1Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #14C[C@@H](O)CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3580.0Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #15C[C@@H](O)CCC[C@H](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)C3589.3Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #16C[C@@H](O)CCC[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)O[Si](C)(C)C(C)(C)C3580.5Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #2C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C(C)(C)C3724.8Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #3C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C(C)(C)C3682.5Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #4C[C@H](CCC[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)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3603.6Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #5C[C@H](CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3587.4Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #6C[C@H](CCC[C@H](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)C)O[Si](C)(C)C(C)(C)C3593.1Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #7C[C@H](CCC[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)O)O[Si](C)(C)C(C)(C)C3588.7Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #8C[C@H](CCC[C@H](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)O[Si](C)(C)C(C)(C)C3660.5Semi standard non polar33892256
19-Hydroxy-PGE2,3TBDMS,isomer #9C[C@H](CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3593.4Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #1C[C@H](CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3805.7Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #2C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C(C)(C)C3800.6Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #3C[C@H](CCC[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)O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3803.3Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #4C[C@H](CCC[C@@H](/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)C)O[Si](C)(C)C(C)(C)C3872.5Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #5C[C@H](CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3806.0Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #6C[C@H](CCC[C@H](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)C)O[Si](C)(C)C(C)(C)C3788.1Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #7C[C@H](CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3794.1Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #8C[C@@H](O)CCC[C@@H](/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)C3771.5Semi standard non polar33892256
19-Hydroxy-PGE2,4TBDMS,isomer #9C[C@@H](O)CCC[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)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3761.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 19-Hydroxy-PGE2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ukd-3469000000-6f3dc9fde359e6ab45862017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19-Hydroxy-PGE2 GC-MS (4 TMS) - 70eV, Positivesplash10-0006-5300269000-3058ca019e9a5cc95b342017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19-Hydroxy-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 - 19-Hydroxy-PGE2 10V, Positive-QTOFsplash10-0f89-0009000000-c7f262f4112709c13b352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 20V, Positive-QTOFsplash10-001i-1149000000-edc217aa5d486d5b96752017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 40V, Positive-QTOFsplash10-000i-9631000000-bf199db1c800ca1b08d42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 10V, Negative-QTOFsplash10-014j-0009000000-10ab06af383d2de195492017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 20V, Negative-QTOFsplash10-052b-0019000000-c91e6c0d4830ae03416e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 40V, Negative-QTOFsplash10-0a4i-9543000000-38127619147a1aa599712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 10V, Negative-QTOFsplash10-0002-0009000000-8303eeea1fd33ad9b2752021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 20V, Negative-QTOFsplash10-001j-0049000000-31de83b614a614e519ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 40V, Negative-QTOFsplash10-053u-9340000000-225c882e6bf0332d16632021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 10V, Positive-QTOFsplash10-001i-0009000000-3d40e65042945aec3b9a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 20V, Positive-QTOFsplash10-001i-1396000000-4eac31344a54707e648e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19-Hydroxy-PGE2 40V, Positive-QTOFsplash10-000i-5910000000-dc43044fc214e02be8b42021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022733
KNApSAcK IDNot Available
Chemspider ID4446165
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283038
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. Oliw EH, Johnsen O: Rapid and slow hydroxylators of seminal E prostaglandins. Biochim Biophys Acta. 1988 Nov 25;963(2):295-301. [PubMed:3196735 ]
  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 ]
  3. Woodward DF, Protzman CE, Krauss AH, Williams LS: Identification of 19 (R)-OH prostaglandin E2 as a selective prostanoid EP2-receptor agonist. Prostaglandins. 1993 Oct;46(4):371-83. [PubMed:8248550 ]
  4. Kelly RW, Taylor PL, Hearn JP, Short RV, Martin DE, Marston JH: 19-Hydroxyprostaglandin E1 as a major component of the semen of primates. Nature. 1976 Apr 8;260(5551):544-5. [PubMed:817207 ]