5-(2-Fluoro-5-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]-1-propen-1-yl}phenyl)-1,2-oxazole-3-carboxylic acid

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
5-(2-Fluoro-5-{(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]-1-propen-1-yl}phenyl)-1,2-oxazole-3-carboxylic acid
Accession Number
DB02014  (EXPT00090)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 5-{2-fluoro-5-[3-(3-hydroxy-2-methoxycarbonyl-phenoxy)-propenyl]-phenyl}-isoxazole-3-carboxylic acid
External IDs
Compound 9
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 413.3526
Monoisotopic: 413.091080076
Chemical Formula
C21H16FNO7
InChI Key
QKHWJUMLYAYZFS-ONEGZZNKSA-N
InChI
InChI=1S/C21H16FNO7/c1-28-21(27)19-16(24)5-2-6-17(19)29-9-3-4-12-7-8-14(22)13(10-12)18-11-15(20(25)26)23-30-18/h2-8,10-11,24H,9H2,1H3,(H,25,26)/b4-3+
IUPAC Name
5-{2-fluoro-5-[(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl]phenyl}-1,2-oxazole-3-carboxylic acid
SMILES
COC(=O)C1=C(O)C=CC=C1OC\C=C\C1=CC(C2=CC(=NO2)C(O)=O)=C(F)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTyrosine-protein phosphatase non-receptor type 1Not 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
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
447994
PubChem Substance
46506116
ChemSpider
394932
BindingDB
13990
ChEMBL
CHEMBL117869
HET
234
PDB Entries
1q1m

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 Solubility0.0337 mg/mLALOGPS
logP4.29ALOGPS
logP4.62ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)3.9ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.09 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity105.01 m3·mol-1ChemAxon
Polarizability40.09 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7297
Caco-2 permeable-0.5448
P-glycoprotein substrateNon-substrate0.6615
P-glycoprotein inhibitor INon-inhibitor0.8081
P-glycoprotein inhibitor IINon-inhibitor0.6613
Renal organic cation transporterNon-inhibitor0.861
CYP450 2C9 substrateNon-substrate0.8062
CYP450 2D6 substrateNon-substrate0.8288
CYP450 3A4 substrateNon-substrate0.5562
CYP450 1A2 substrateInhibitor0.5936
CYP450 2C9 inhibitorInhibitor0.6453
CYP450 2D6 inhibitorNon-inhibitor0.883
CYP450 2C19 inhibitorInhibitor0.6329
CYP450 3A4 inhibitorNon-inhibitor0.583
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7756
Ames testNon AMES toxic0.6832
CarcinogenicityNon-carcinogens0.8545
BiodegradationNot ready biodegradable0.9901
Rat acute toxicity2.4032 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9556
hERG inhibition (predictor II)Non-inhibitor0.8719
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 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 o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
o-Hydroxybenzoic acid esters
Alternative Parents
Salicylic acid and derivatives / Styrenes / Phenoxy compounds / Phenol ethers / Benzoyl derivatives / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Alkyl aryl ethers / Fluorobenzenes / Aryl fluorides
show 13 more
Substituents
O-hydroxybenzoic acid ester / Salicylic acid or derivatives / Phenoxy compound / Benzoyl / Phenol ether / Styrene / Alkyl aryl ether / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Fluorobenzene
show 27 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Tyrosine-protein phosphatase which acts as a regulator of endoplasmic reticulum unfolded protein response. Mediates dephosphorylation of EIF2AK3/PERK; inactivating the protein kinase activity of EI...
Gene Name
PTPN1
Uniprot ID
P18031
Uniprot Name
Tyrosine-protein phosphatase non-receptor type 1
Molecular Weight
49966.44 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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 June 13, 2005 07:24 / Updated on June 04, 2019 05:26