2-[(2,4-DICHLOROBENZOYL)AMINO]-5-(PYRIMIDIN-2-YLOXY)BENZOIC ACID
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Identification
- Generic Name
- 2-[(2,4-DICHLOROBENZOYL)AMINO]-5-(PYRIMIDIN-2-YLOXY)BENZOIC ACID
- DrugBank Accession Number
- DB08402
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 404.204
Monoisotopic: 403.012661269 - Chemical Formula
- C18H11Cl2N3O4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPeroxisome proliferator-activated receptor gamma Not Available Humans UNuclear receptor coactivator 2 Not Available Humans URetinoic acid receptor RXR-alpha 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 benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Benzanilides
- Alternative Parents
- Diarylethers / 4-halobenzoic acids and derivatives / 2-halobenzoic acids and derivatives / Benzoic acids / Benzamides / Benzoyl derivatives / Dichlorobenzenes / Phenoxy compounds / Phenol ethers / Aryl chlorides show 13 more
- Substituents
- 1,3-dichlorobenzene / 2-halobenzoic acid or derivatives / 4-halobenzoic acid or derivatives / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzamide / Benzanilide / Benzoic acid show 28 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organochlorine compound, amidobenzoic acid, aryloxypyrimidine (CHEBI:47621)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- VNDRRWBKNSHALL-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H11Cl2N3O4/c19-10-2-4-12(14(20)8-10)16(24)23-15-5-3-11(9-13(15)17(25)26)27-18-21-6-1-7-22-18/h1-9H,(H,23,24)(H,25,26)
- IUPAC Name
- 2-(2,4-dichlorobenzamido)-5-(pyrimidin-2-yloxy)benzoic acid
- SMILES
- OC(=O)C1=C(NC(=O)C2=C(Cl)C=C(Cl)C=C2)C=CC(OC2=NC=CC=N2)=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5289162
- PubChem Substance
- 99444873
- ChemSpider
- 4451178
- ChEMBL
- CHEMBL1204498
- ZINC
- ZINC000012358153
- PDBe Ligand
- PLB
- PDB Entries
- 1wm0 / 2q6s / 3dzu / 8zfn / 8zfq
Clinical Trials
- Clinical Trials
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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 0.0128 mg/mL ALOGPS logP 3.28 ALOGPS logP 4.84 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 3.28 Chemaxon pKa (Strongest Basic) 0.97 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 101.41 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 101.31 m3·mol-1 Chemaxon Polarizability 37.66 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.5491 Blood Brain Barrier + 0.7588 Caco-2 permeable - 0.6468 P-glycoprotein substrate Non-substrate 0.7676 P-glycoprotein inhibitor I Non-inhibitor 0.8796 P-glycoprotein inhibitor II Non-inhibitor 0.9281 Renal organic cation transporter Non-inhibitor 0.9211 CYP450 2C9 substrate Non-substrate 0.7293 CYP450 2D6 substrate Non-substrate 0.8762 CYP450 3A4 substrate Non-substrate 0.6154 CYP450 1A2 substrate Non-inhibitor 0.5876 CYP450 2C9 inhibitor Non-inhibitor 0.9334 CYP450 2D6 inhibitor Non-inhibitor 0.8928 CYP450 2C19 inhibitor Non-inhibitor 0.8655 CYP450 3A4 inhibitor Non-inhibitor 0.8681 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7005 Ames test Non AMES toxic 0.9017 Carcinogenicity Non-carcinogens 0.8647 Biodegradation Not ready biodegradable 0.9626 Rat acute toxicity 2.0475 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9565 hERG inhibition (predictor II) Non-inhibitor 0.8232
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-1911000000-44bdfeb2ddb88ffe0b5f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0fk9-0900400000-feeaa748dbe395697f82 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0227900000-165f47e6945e2895d527 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0309200000-9a975da1fd194d810628 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f8a-7119100000-370e6ecc225543292b1c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0fmi-0739000000-f7512417cb7abf9888db Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-134b6e535a0e7b620916 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]- 187.86916 predictedDeepCCS 1.0 (2019) [M+H]+ 190.22716 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.8318 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated pro-inflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of BMAL1 in the blood vessels (By similarity)
- Specific Function
- alpha-actinin binding
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 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]
2. DetailsNuclear receptor coactivator 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcriptional coactivator for steroid receptors and nuclear receptors (PubMed:23508108, PubMed:8670870, PubMed:9430642). Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1) (PubMed:23508108, PubMed:8670870, PubMed:9430642). Required with NCOA1 to control energy balance between white and brown adipose tissues (PubMed:23508108, PubMed:8670870, PubMed:9430642). Critical regulator of glucose metabolism regulation, acts as a RORA coactivator to specifically modulate G6PC1 expression (PubMed:23508108, PubMed:8670870, PubMed:9430642). Involved in the positive regulation of the transcriptional activity of the glucocorticoid receptor NR3C1 by sumoylation enhancer RWDD3 (PubMed:23508108). Positively regulates the circadian clock by acting as a transcriptional coactivator for the CLOCK-BMAL1 heterodimer (By similarity)
- Specific Function
- aryl hydrocarbon receptor binding
- Gene Name
- NCOA2
- Uniprot ID
- Q15596
- Uniprot Name
- Nuclear receptor coactivator 2
- Molecular Weight
- 159155.645 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]
3. DetailsRetinoic acid receptor RXR-alpha
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor for retinoic acid that acts as a transcription factor (PubMed:11162439, PubMed:11915042, PubMed:37478846). Forms homo- or heterodimers with retinoic acid receptors (RARs) and binds to target response elements in response to their ligands, all-trans or 9-cis retinoic acid, to regulate gene expression in various biological processes (PubMed:10195690, PubMed:11162439, PubMed:11915042, PubMed:16107141, PubMed:17761950, PubMed:18800767, PubMed:19167885, PubMed:28167758, PubMed:37478846). The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 to regulate transcription (PubMed:10195690, PubMed:11162439, PubMed:11915042, PubMed:17761950, PubMed:28167758). The high affinity ligand for retinoid X receptors (RXRs) is 9-cis retinoic acid (PubMed:1310260). In the absence of ligand, the RXR-RAR heterodimers associate with a multiprotein complex containing transcription corepressors that induce histone deacetylation, chromatin condensation and transcriptional suppression (PubMed:20215566). On ligand binding, the corepressors dissociate from the receptors and coactivators are recruited leading to transcriptional activation (PubMed:20215566, PubMed:37478846, PubMed:9267036). Serves as a common heterodimeric partner for a number of nuclear receptors, such as RARA, RARB and PPARA (PubMed:10195690, PubMed:11915042, PubMed:28167758, PubMed:29021580). The RXRA/RARB heterodimer can act as a transcriptional repressor or transcriptional activator, depending on the RARE DNA element context (PubMed:29021580). The RXRA/PPARA heterodimer is required for PPARA transcriptional activity on fatty acid oxidation genes such as ACOX1 and the P450 system genes (PubMed:10195690). Together with RARA, positively regulates microRNA-10a expression, thereby inhibiting the GATA6/VCAM1 signaling response to pulsatile shear stress in vascular endothelial cells (PubMed:28167758). Acts as an enhancer of RARA binding to RARE DNA element (PubMed:28167758). May facilitate the nuclear import of heterodimerization partners such as VDR and NR4A1 (PubMed:12145331, PubMed:15509776). Promotes myelin debris phagocytosis and remyelination by macrophages (PubMed:26463675). Plays a role in the attenuation of the innate immune system in response to viral infections, possibly by negatively regulating the transcription of antiviral genes such as type I IFN genes (PubMed:25417649). Involved in the regulation of calcium signaling by repressing ITPR2 gene expression, thereby controlling cellular senescence (PubMed:30216632)
- Specific Function
- DNA binding domain binding
- Gene Name
- RXRA
- Uniprot ID
- P19793
- Uniprot Name
- Retinoic acid receptor RXR-alpha
- Molecular Weight
- 50810.835 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 21:31 / Updated at June 12, 2020 16:52