Showing metabocard for 20-Hydroxy-PGE2 (BMDB0003247)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:03:19 UTC
Update Date2020-04-22 15:11:53 UTC
BMDB IDBMDB0003247
Secondary Accession Numbers
  • BMDB03247
Metabolite Identification
Common Name20-Hydroxy-PGE2
Description20-Hydroxy-PGE2, also known as 20-OH-pge2, 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. Thus, 20-hydroxy-pge2 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 20-Hydroxy-PGE2.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(5Z,11alpha,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oic acidChEBI
20-Hydroxy prostaglandin e2ChEBI
20-Hydroxy-prostaglandin e2ChEBI
20-OH-PGE2ChEBI
9-oxo-11R,15S,20-Trihydroxy-5Z,13E-prostadienoic acidChEBI
(5Z,11a,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11a,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,11alpha,13E,15S)-11,15,20-Trihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15,20-trihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15,20-trihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
9-oxo-11R,15S,20-Trihydroxy-5Z,13E-prostadienoateGenerator
(5Z,11(alpha),13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-OateHMDB
(5Z,11(alpha),13E,15S)-11,15-Dihydroxy-9-oxo-prosta-5,13-dien-1-Oic acidHMDB
20-Hydroxyprostaglandin e2HMDB
20-Hydroxy-pge2ChEBI
Chemical FormulaC20H32O6
Average Molecular Weight368.4645
Monoisotopic Molecular Weight368.219888756
IUPAC Name(5Z)-7-[(1R,2R,3R)-2-[(1E,3S)-3,8-dihydroxyoct-1-en-1-yl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic acid
Traditional Name20-Hydroxy-PGE2
CAS Registry Number57930-95-7
SMILES
OCCCCC[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/c21-13-7-3-4-8-15(22)11-12-17-16(18(23)14-19(17)24)9-5-1-2-6-10-20(25)26/h1,5,11-12,15-17,19,21-22,24H,2-4,6-10,13-14H2,(H,25,26)/b5-1-,12-11+/t15-,16+,17+,19+/m0/s1
InChI KeyAZIGEYVZEVXWAD-NZGURKHLSA-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
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.02ALOGPS
logP1.79ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.06 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity101.36 m³·mol⁻¹ChemAxon
Polarizability41.56 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udv-2496000000-99122637177145628ab2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0006-9300368000-b5e56740df85f5d1a0a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0009000000-ebd1464d44ae0ca6b6a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0149000000-230b542bf2b718260276View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9531000000-fe0172c7250e86fb8008View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0009000000-de1b715838573884563eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kb-0019000000-173f7be02a65564b8220View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9443000000-589d4f940035f349cf6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0009000000-ab61e9dbf0bdcec01a2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001r-2498000000-dd316fed2942370b1a27View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5900000000-a1dd05387d766559f669View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00l2-0009000000-34934b7cf26c41e47d90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0049000000-440e860b86a5284b8bccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-8973000000-deffc6d4dd2cd22e8a50View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0003247
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023129
KNApSAcK IDNot Available
Chemspider ID4446161
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3814
PubChem Compound5283034
PDB IDNot Available
ChEBI ID137370
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available