5-(3-{3-[3-HYDROXY-2-(METHOXYCARBONYL)PHENOXY]PROPENYL}PHENYL)-4-(HYDROXYMETHYL)ISOXAZOLE-3-CARBOXYLIC ACID
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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
Target Actions Organism UTyrosine-protein phosphatase non-receptor type 1 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- External Links
- PubChem Compound
- 449162
- PubChem Substance
- 99444472
- ChemSpider
- 395769
- BindingDB
- 13997
- ChEMBL
- CHEMBL184444
- ZINC
- ZINC000014954269
- PDBe Ligand
- IX1
- PDB Entries
- 1xbo
Clinical Trials
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
Property Value Source Water Solubility 0.0662 mg/mL ALOGPS logP 3.65 ALOGPS logP 3.71 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 3.86 Chemaxon pKa (Strongest Basic) -3.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 139.32 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 111.61 m3·mol-1 Chemaxon Polarizability 42.57 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9956 Blood Brain Barrier + 0.5914 Caco-2 permeable - 0.5967 P-glycoprotein substrate Non-substrate 0.6121 P-glycoprotein inhibitor I Non-inhibitor 0.8292 P-glycoprotein inhibitor II Inhibitor 0.5978 Renal organic cation transporter Non-inhibitor 0.8081 CYP450 2C9 substrate Non-substrate 0.7226 CYP450 2D6 substrate Non-substrate 0.8341 CYP450 3A4 substrate Non-substrate 0.5645 CYP450 1A2 substrate Non-inhibitor 0.5928 CYP450 2C9 inhibitor Inhibitor 0.6368 CYP450 2D6 inhibitor Non-inhibitor 0.8557 CYP450 2C19 inhibitor Inhibitor 0.5769 CYP450 3A4 inhibitor Inhibitor 0.5891 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7979 Ames test Non AMES toxic 0.706 Carcinogenicity Non-carcinogens 0.8729 Biodegradation Not ready biodegradable 0.7454 Rat acute toxicity 2.3650 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9248 hERG inhibition (predictor II) Non-inhibitor 0.8602
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-002r-0904000000-2c5b5a3b24f61cdb327d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000j-0609000000-0700ed1a416355ad77c4 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-054o-0196000000-842cfa3ca2ebedaf2de1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-06ri-0907000000-912b53d94227c03f9405 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0798200000-417217a9b79d875b612e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4l-1129000000-194a1f2af95871c7ff9c Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 197.16173 predictedDeepCCS 1.0 (2019) [M+H]+ 199.5573 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.49776 predictedDeepCCS 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
- 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