15-Deoxy-d-12,14-PGJ2 (CHEM021700)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:10:23 UTC
Update Date2016-11-09 01:17:20 UTC
Accession NumberCHEM021700
Identification
Common Name15-Deoxy-d-12,14-PGJ2
ClassSmall Molecule
DescriptionA prostaglandin J derivative comprising prostaglandin J2 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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-Delta12,14-prostaglandin J2Kegg
15-Deoxy-δ-12,14-PGJ2Generator
15-Deoxy-δ-12,14-prostaglandin J2Generator
Δ-12,14-15-deoxy-PGJ2Generator
15-Deoxy-δ12,14-prostaglandin J2Generator
(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 J2HMDB
15-Deoxy-delta(12,14)-prostaglandin J2HMDB
15-Deoxy-12,14-prostaglandin J2HMDB
15-Deoxy-delta(12,14)PGJ2HMDB
Chemical FormulaC20H28O3
Average Molecular Mass316.435 g/mol
Monoisotopic Mass316.204 g/mol
CAS Registry Number87893-55-8
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
SMILESCCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O
InChI IdentifierInChI=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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability37.49 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-6290000000-3dc60f4b59ef5f20d684Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-007c-9352000000-0ced364db9c5f3e628e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0294000000-a09703fda20ef890154eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-2590000000-7a0889bba7bd7ec5abd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9410000000-6716fa5d4535af90b53bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-1568a862c2a207983dd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1297000000-85bb29f3a42e11f9c53aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9520000000-05e5fcf470c134176904Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-1292000000-b96f27a7a0fb5f4a4574Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9730000000-e86765cb72eecd2feb8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05rr-9500000000-43060ace2e2f26804b0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-c1967ca10292a13ad947Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-0294000000-ecdf0c0084d7f716f9a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-1930000000-dd5d68b51f67954b6ba6Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005079
FooDB IDFDB112223
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4470730
ChEBI ID34159
PubChem Compound ID5311211
Kegg Compound IDC14717
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10917568
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=11030710
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=11872377
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=11961117
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12032289
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12970094
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=15487891
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=15694358
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15750045
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15821150
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=15843042
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16413037
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=16795079
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=17074064
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=17074304
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=18278062
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=18367541
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=18671867
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=19050284
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=19299483
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=19494510
22. Bickley, 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.
23. Bickley, 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.
24. 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.
25. 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.
26. 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.
27. Lipid Maps (LMFA03010021): http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA03010021