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

Identification

Generic Name
5-(3-{3-[3-HYDROXY-2-(METHOXYCARBONYL)PHENOXY]PROPENYL}PHENYL)-4-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLIC ACID
DrugBank Accession Number
DB08001
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 425.3882
Monoisotopic: 425.111066589
Chemical Formula
C22H19NO8
Synonyms
Not Available

Pharmacology

Indication

Not Available

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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

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 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
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzoyl / Carboxylic acid
show 24 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
449162
PubChem Substance
99444472
ChemSpider
395769
BindingDB
13997
ChEMBL
CHEMBL184444
ZINC
ZINC000014954269
PDBe Ligand
IX1
PDB Entries
1xbo

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 Solubility0.0662 mg/mLALOGPS
logP3.65ALOGPS
logP3.71Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.86Chemaxon
pKa (Strongest Basic)-3.1Chemaxon
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/MSsplash10-002r-0904000000-2c5b5a3b24f61cdb327d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-0609000000-0700ed1a416355ad77c4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-054o-0196000000-842cfa3ca2ebedaf2de1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06ri-0907000000-912b53d94227c03f9405
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gb9-0798200000-417217a9b79d875b612e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4l-1129000000-194a1f2af95871c7ff9c
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]-197.16173
predicted
DeepCCS 1.0 (2019)
[M+H]+199.5573
predicted
DeepCCS 1.0 (2019)
[M+Na]+205.49776
predicted
DeepCCS 1.0 (2019)

Targets

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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. [Article]

Drug created at September 15, 2010 21:27 / Updated at June 12, 2020 16:52