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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-10-25 09:59:41 UTC
Update Date2019-07-23 05:46:43 UTC
HMDB IDHMDB0005079
Secondary Accession Numbers
  • HMDB05079
Metabolite Identification
Common Name15-Deoxy-d-12,14-PGJ2
Description15-deoxy-PGJ2 (15d-PGJ2) is a metabolite of the PGJ2 prostanoid family that influences multiple signaling pathways by covalently binding with key signaling molecules. Among them, 15d-PGJ2 has displayed highest potency as an inducer of gene expression. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207 , 16857669 ). 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?1563860803
Synonyms
ValueSource
15-Deoxy-delta-12,14-PGJ2ChEBI
15-Deoxy-delta-12,14-prostaglandin J2ChEBI
15-Deoxy-PGJ2ChEBI
delta-12,14-15-Deoxy-PGJ2ChEBI
15-Deoxy-δ-12,14-PGJ2Generator
15-Deoxy-δ-12,14-prostaglandin J2Generator
δ-12,14-15-deoxy-PGJ2Generator
(5Z,12E,14E) 11-oxo Prosta-5,9,12,14-tetraen-1-OateHMDB
(5Z,12E,14E) 11-oxo Prosta-5,9,12,14-tetraen-1-Oic acidHMDB
(5Z,12E,14E)-11-oxo-Prosta-5,9,12,14-tetraen-1-OateHMDB
(5Z,12E,14E)-11-oxo-Prosta-5,9,12,14-tetraen-1-Oic acidHMDB
11-oxo-5Z,9,12,14-ProstatetraenoateHMDB
11-oxo-5Z,9,12,14-Prostatetraenoic acidHMDB
15-Deoxy-delta 12, 14-prostaglandin J2HMDB
15-Deoxy-delta-12, 14 PGJ-2HMDB
15-Deoxy-delta12,14-PGJ2HMDB
15-Deoxy-delta12,14-prostaglandinHMDB
15-Deoxy-prostaglandin J2HMDB
15D-PGJ2HMDB
Delta12,14-PGJ2HMDB
15-Deoxyprostaglandin J2MeSH
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name(5Z)-7-[(1S,5E)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
Traditional Namedelta12,14-PGJ2
CAS Registry Number87893-55-8
SMILES
CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O
InChI Identifier
InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1
InChI KeyVHRUMKCAEVRUBK-GODQJPCRSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 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 homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.983Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP5.39ALOGPS
logP5.46ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.66ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity98.45 m³·mol⁻¹ChemAxon
Polarizability37.53 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6290000000-3dc60f4b59ef5f20d684JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007c-9352000000-0ced364db9c5f3e628e4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0294000000-a09703fda20ef890154eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-2590000000-7a0889bba7bd7ec5abd5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9410000000-6716fa5d4535af90b53bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-1568a862c2a207983dd6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1297000000-85bb29f3a42e11f9c53aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9520000000-05e5fcf470c134176904JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000083 +/- 0.000003 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.000206 +/- 0.000011 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified<0.0003 uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0000023 +/- 0.000001 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.00005 +/- 0.000018 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected and Quantified0.000018 +/- 0.000004 umol/mmol creatinineAdult (>18 years old)MaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023619
KNApSAcK IDNot Available
Chemspider ID4470730
KEGG Compound IDC14717
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5311211
PDB IDNot Available
ChEBI ID34159
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceBickley, Jamie F.; Jadhav, Vasudev; Roberts, Stanley M.; Santoro, M. Gabriella; Steiner, Alexander; Sutton, Peter W. Synthesis of optically active prostaglandin-J2 and 15-deoxy-D12,14-prostaglandin-J2. Synlett (2003), (8), 1170-1174.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yu X, Egner PA, Wakabayashi J, Wakabayashi N, Yamamoto M, Kensler TW: Nrf2-mediated induction of cytoprotective enzymes by 15-deoxy-Delta12,14-prostaglandin J2 is attenuated by alkenal/one oxidoreductase. J Biol Chem. 2006 Sep 8;281(36):26245-52. Epub 2006 Jul 20. [PubMed:16857669 ]
  2. Masoodi M, Nicolaou A: Lipidomic analysis of twenty-seven prostanoids and isoprostanes by liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(20):3023-9. [PubMed:16986207 ]
  3. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  4. Lipid Maps (LMFA03010021) [Link]