Record Information
Version1.0
Creation date2015-05-07 18:39:48 UTC
Update date2019-11-26 03:21:36 UTC
Primary IDFDB030125
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate
Description(5z)-(15s)-11-α-hydroxy-9,15-dioxoprosta-13-enoate, also known as 15-dehydro-prostaglandin e2 anion, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds 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 (5z)-(15s)-11-α-hydroxy-9,15-dioxoprosta-13-enoate is practically insoluble (in water) and a weakly acidic compound (based on its pKa). (5z)-(15s)-11-α-hydroxy-9,15-dioxoprosta-13-enoate can be found in a number of food items such as maitake, green zucchini, yellow pond-lily, and canada blueberry, which makes (5z)-(15s)-11-α-hydroxy-9,15-dioxoprosta-13-enoate a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
15-Dehydro-prostaglandin e2 anionChEBI
15-Oxoprostaglandin e2ChEBI
15-oxo-Prostaglandin e2ChEBI
9,15-dioxo-11-Hydroxyprosta-5,13-dienoic acidMeSH
15-keto-PGE2MeSH
15-keto-Prostaglandin e2MeSH
15-Ketoprostaglandin e2MeSH
15-oxo-PGE2MeSH
15-Ketoprostaglandin e2, (11alpha)-isomerMeSH
(5Z)-(15S)-11-Α-hydroxy-9,15-dioxoprosta-13-enoic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.034 g/LALOGPS
logP3.1ALOGPS
logP3.64ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)4.3ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area94.5 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity109.37 m³·mol⁻¹ChemAxon
Polarizability38.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H29O5
IUPAC name(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoate
InChI IdentifierInChI=1S/C20H30O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/p-1/b7-4-,13-12+/t16-,17-,19-/m1/s1
InChI KeyYRTJDWROBKPZNV-KMXMBPPJSA-M
Isomeric SMILES[H]\C(CCCC([O-])=O)=C(/[H])C[C@@]1([H])C(=O)C[C@@]([H])(O)[C@]1([H])C(\[H])=C(/[H])C(=O)CCCCC
Average Molecular Weight349.448
Monoisotopic Molecular Weight349.202047614
Classification
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
  • Acryloyl-group
  • Cyclic alcohol
  • Alpha,beta-unsaturated ketone
  • Enone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0019000000-4b5e646d04659c2c3cb3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1069000000-c24e5e2522c6cfb1a335Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-3692000000-fcb17f198cb61153d7e6Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference