(5E,14E)-11-oxoprosta-5,9,12,14-tetraen-1-oic acid

Identification

Name
(5E,14E)-11-oxoprosta-5,9,12,14-tetraen-1-oic acid
Accession Number
DB08435
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 316.4345
Monoisotopic: 316.203844762
Chemical Formula
C20H28O3
InChI Key
VHRUMKCAEVRUBK-XOVNXQNQSA-N
InChI
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
IUPAC Name
(5E)-7-[(1S,5Z)-5-[(2E)-oct-2-en-1-ylidene]-4-oxocyclopent-2-en-1-yl]hept-5-enoic acid
SMILES
[H][[email protected]]1(C\C=C\CCCC(O)=O)C=CC(=O)\C1=C/C=C/CCCCC

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor gammaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
23654841
PubChem Substance
99444906
ChemSpider
25029186
ChEMBL
CHEMBL1210221
HET
PTG
PDB Entries
2zk1 / 2zk2 / 2zvt

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity98.45 m3·mol-1ChemAxon
Polarizability37.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.8172
Caco-2 permeable+0.658
P-glycoprotein substrateSubstrate0.5363
P-glycoprotein inhibitor INon-inhibitor0.7656
P-glycoprotein inhibitor IINon-inhibitor0.9518
Renal organic cation transporterNon-inhibitor0.8737
CYP450 2C9 substrateNon-substrate0.8328
CYP450 2D6 substrateNon-substrate0.8983
CYP450 3A4 substrateSubstrate0.5155
CYP450 1A2 substrateNon-inhibitor0.8969
CYP450 2C9 inhibitorNon-inhibitor0.9323
CYP450 2D6 inhibitorNon-inhibitor0.896
CYP450 2C19 inhibitorNon-inhibitor0.8602
CYP450 3A4 inhibitorNon-inhibitor0.9035
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.927
Ames testNon AMES toxic0.9312
CarcinogenicityNon-carcinogens0.9231
BiodegradationReady biodegradable0.8969
Rat acute toxicity2.1745 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8324
hERG inhibition (predictor II)Non-inhibitor0.8893
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Eicosanoids
Direct Parent
Prostaglandins and related compounds
Alternative Parents
Long-chain fatty acids / Unsaturated fatty acids / Cyclic ketones / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
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
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:31 / Updated on December 01, 2017 16:04