5-(3-{3-[3-HYDROXY-2-(METHOXYCARBONYL)PHENOXY]PROPENYL}PHENYL)-4-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLIC ACID

Identification

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Name
5-(3-{3-[3-HYDROXY-2-(METHOXYCARBONYL)PHENOXY]PROPENYL}PHENYL)-4-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLIC ACID
Accession Number
DB08001
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: 425.3882
Monoisotopic: 425.111066589
Chemical Formula
C22H19NO8
InChI Key
DQSRCEFDWMQCCV-GQCTYLIASA-N
InChI
InChI=1S/C22H19NO8/c1-29-22(28)18-16(25)8-3-9-17(18)30-10-4-6-13-5-2-7-14(11-13)20-15(12-24)19(21(26)27)23-31-20/h2-9,11,24-25H,10,12H2,1H3,(H,26,27)/b6-4+
IUPAC Name
5-{3-[(1E)-3-[3-hydroxy-2-(methoxycarbonyl)phenoxy]prop-1-en-1-yl]phenyl}-4-(hydroxymethyl)-1,2-oxazole-3-carboxylic acid
SMILES
COC(=O)C1=C(O)C=CC=C1OC\C=C\C1=CC(=CC=C1)C1=C(CO)C(=NO1)C(O)=O

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
449162
PubChem Substance
99444472
ChemSpider
395769
BindingDB
13997
ChEMBL
CHEMBL184444
HET
IX1
PDB Entries
1xbo

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 Solubility0.0662 mg/mLALOGPS
logP3.65ALOGPS
logP3.71ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.86ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.32 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.61 m3·mol-1ChemAxon
Polarizability42.57 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9956
Blood Brain Barrier+0.5914
Caco-2 permeable-0.5967
P-glycoprotein substrateNon-substrate0.6121
P-glycoprotein inhibitor INon-inhibitor0.8292
P-glycoprotein inhibitor IIInhibitor0.5978
Renal organic cation transporterNon-inhibitor0.8081
CYP450 2C9 substrateNon-substrate0.7226
CYP450 2D6 substrateNon-substrate0.8341
CYP450 3A4 substrateNon-substrate0.5645
CYP450 1A2 substrateNon-inhibitor0.5928
CYP450 2C9 inhibitorInhibitor0.6368
CYP450 2D6 inhibitorNon-inhibitor0.8557
CYP450 2C19 inhibitorInhibitor0.5769
CYP450 3A4 inhibitorInhibitor0.5891
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7979
Ames testNon AMES toxic0.706
CarcinogenicityNon-carcinogens0.8729
BiodegradationNot ready biodegradable0.7454
Rat acute toxicity2.3650 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9248
hERG inhibition (predictor II)Non-inhibitor0.8602
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 / Benzoyl derivatives / Phenol ethers / Phenoxy compounds / Styrenes / 1-hydroxy-4-unsubstituted benzenoids / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Dicarboxylic acids and derivatives / Vinylogous acids
show 12 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 / Phenol
show 24 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. 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 15:27 / Updated on June 04, 2019 06:50