PGH3 (CHEM041081)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:11:20 UTC
Update Date2016-11-09 01:22:23 UTC
Accession NumberCHEM041081
Identification
Common NamePGH3
ClassSmall Molecule
DescriptionA member of the class of prostaglandins H that is 9,11-epidioxyprosta-5,13,17-trienoic acid carrying an additional hydroxy substituent at the 15S-position.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(5Z,9alpha,11alpha,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-Oic acidChEBI
(5Z,9S,11R,13E,15S,17Z)-15-Hydroxy-9,11-epidioxyprosta-5,13,17-trienoic acidChEBI
PGH3ChEBI
(5Z,9a,11a,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-OateGenerator
(5Z,9a,11a,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-Oic acidGenerator
(5Z,9alpha,11alpha,13E,15S,17Z)-9,11-Epidioxy-15-hydroxyprosta-5,13,17-trien-1-OateGenerator
(5Z,9Α,11α,13E,15S,17Z)-9,11-epidioxy-15-hydroxyprosta-5,13,17-trien-1-OateGenerator
(5Z,9Α,11α,13E,15S,17Z)-9,11-epidioxy-15-hydroxyprosta-5,13,17-trien-1-Oic acidGenerator
(5Z,9S,11R,13E,15S,17Z)-15-Hydroxy-9,11-epidioxyprosta-5,13,17-trienoateGenerator
Chemical FormulaC20H30O5
Average Molecular Mass350.449 g/mol
Monoisotopic Mass350.209 g/mol
CAS Registry NumberNot Available
IUPAC Name(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
Traditional Name(5Z)-7-[(1R,4S,5R,6R)-6-[(1E,3S,5Z)-3-hydroxyocta-1,5-dien-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
SMILESCC\C=C/C[C@@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O
InChI IdentifierInChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h3-4,6-7,12-13,15-19,21H,2,5,8-11,14H2,1H3,(H,22,23)/b6-3-,7-4-,13-12+/t15-,16-,17-,18+,19-/m1/s1
InChI KeyPVTQTOGPOPGQGE-LWAFXZDQSA-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
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Ortho-dioxane
  • Fatty acid
  • Unsaturated fatty acid
  • Ortho-dioxolane
  • Dialkyl peroxide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.041 g/LALOGPS
logP4.22ALOGPS
logP3.6ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity99.16 m³·mol⁻¹ChemAxon
Polarizability38.71 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0019000000-77e67e33d78d860c2b69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-067r-5197000000-a340b5689ff35749ead6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-9300000000-3f5fdbb50eb4e2f4786eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0019000000-15c30c1364eb62a11cdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-3294000000-c385acec093995b9b2ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9700000000-953ce8ec5b904f32214eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-0009000000-d5a90b83be9f7c55e538Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0039000000-9792e0648327259104ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-5293000000-1bd1d88436ef3645370fSpectrum
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 IDHMDB0013040
FooDB IDFDB029265
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID52085727
ChEBI ID134407
PubChem Compound ID101600091
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=2491846
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=3579292
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=531219
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=6966885
5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
9. The lipid handbook with CD-ROM