NAV

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

Identification

Generic Name
(5E,14E)-11-oxoprosta-5,9,12,14-tetraen-1-oic acid
DrugBank Accession Number
DB08435
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 316.4345
Monoisotopic: 316.203844762
Chemical Formula
C20H28O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPeroxisome proliferator-activated receptor gammaNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Aliphatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclic ketone / Fatty acid / Hydrocarbon derivative / Ketone / Long-chain fatty acid / Monocarboxylic acid or derivatives
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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][C@]1(C\C=C\CCCC(O)=O)C=CC(=O)\C1=C/C=C/CCCCC

References

General References
Not Available
PubChem Compound
23654841
PubChem Substance
99444906
ChemSpider
25029186
ChEMBL
CHEMBL1210221
ZINC
ZINC000038139032
PDBe Ligand
PTG
PDB Entries
2zk1 / 2zk2 / 2zvt / 6i5g

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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-MSsplash10-0006-7390000000-8798247eb72414340088
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001j-0190000000-6ee57ac0c7a51b7b5a51
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0039000000-d1ec115eb9fe85c680b4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0291000000-c51e99dabe9186499cf9
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00m1-3970000000-7198c24edd6549f82492
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0089-0960000000-8b463077a73de4dbd44e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00pi-4890000000-3aeca870ed06788864ea
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.56757
predicted
DeepCCS 1.0 (2019)
[M+H]+177.92557
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.06372
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Peroxisome proliferator-activated receptor gamma
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52