ethyl 3-[(E)-2-amino-1-cyanoethenyl]-6,7-dichloro-1-methyl-1H-indole-2-carboxylate
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Identification
- Generic Name
- ethyl 3-[(E)-2-amino-1-cyanoethenyl]-6,7-dichloro-1-methyl-1H-indole-2-carboxylate
- DrugBank Accession Number
- DB08691
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 338.189
Monoisotopic: 337.038482089 - Chemical Formula
- C15H13Cl2N3O2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ADual specificity protein kinase CLK1 inhibitorHumans ADual specificity tyrosine-phosphorylation-regulated kinase 1A inhibitorHumans UDual specificity protein kinase CLK3 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 indolecarboxylic acids and derivatives. These are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Indoles and derivatives
- Sub Class
- Indolecarboxylic acids and derivatives
- Direct Parent
- Indolecarboxylic acids and derivatives
- Alternative Parents
- N-alkylindoles / Indoles / Pyrrole carboxylic acids and derivatives / Aryl chlorides / Benzenoids / N-methylpyrroles / Heteroaromatic compounds / Amino acids and derivatives / Carboxylic acid esters / Azacyclic compounds show 9 more
- Substituents
- Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Carbonitrile / Carboxylic acid derivative / Carboxylic acid ester show 22 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- CXJCGSPAPOTTSF-VURMDHGXSA-N
- InChI
- InChI=1S/C15H13Cl2N3O2/c1-3-22-15(21)14-11(8(6-18)7-19)9-4-5-10(16)12(17)13(9)20(14)2/h4-6H,3,18H2,1-2H3/b8-6-
- IUPAC Name
- ethyl 3-[(1E)-2-amino-1-cyanoeth-1-en-1-yl]-6,7-dichloro-1-methyl-1H-indole-2-carboxylate
- SMILES
- CCOC(=O)C1=C(\C(=C/N)C#N)C2=C(N1C)C(Cl)=C(Cl)C=C2
References
- General References
- Not Available
- External Links
- PubChem Compound
- 44237094
- PubChem Substance
- 99445162
- ChemSpider
- 22378449
- ChEMBL
- CHEMBL1236620
- ZINC
- ZINC000033295985
- PDBe Ligand
- V25
- PDB Entries
- 2vag / 2wu7 / 6qty / 6tw2
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data
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 0.0359 mg/mL ALOGPS logP 3.53 ALOGPS logP 3.01 Chemaxon logS -4 ALOGPS pKa (Strongest Basic) 2.03 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 81.04 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 86.6 m3·mol-1 Chemaxon Polarizability 32.77 Å3 Chemaxon Number of Rings 2 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 + 1.0 Blood Brain Barrier + 0.7796 Caco-2 permeable + 0.5304 P-glycoprotein substrate Non-substrate 0.6472 P-glycoprotein inhibitor I Non-inhibitor 0.8564 P-glycoprotein inhibitor II Inhibitor 0.5494 Renal organic cation transporter Non-inhibitor 0.7794 CYP450 2C9 substrate Non-substrate 0.858 CYP450 2D6 substrate Non-substrate 0.8167 CYP450 3A4 substrate Substrate 0.5486 CYP450 1A2 substrate Inhibitor 0.7823 CYP450 2C9 inhibitor Inhibitor 0.5239 CYP450 2D6 inhibitor Non-inhibitor 0.8938 CYP450 2C19 inhibitor Inhibitor 0.5094 CYP450 3A4 inhibitor Non-inhibitor 0.8132 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9242 Ames test Non AMES toxic 0.5853 Carcinogenicity Non-carcinogens 0.87 Biodegradation Not ready biodegradable 0.9839 Rat acute toxicity 2.6602 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9571 hERG inhibition (predictor II) Non-inhibitor 0.7558
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-004i-6094000000-cf10d28c767884645e52 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-0059000000-3342efe7abb3e2379544 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0098000000-d3fe617642fcfb12e160 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000l-0079000000-c3333dbca61f88dbbba6 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0019-8093000000-6cdd5725dde67c0a53b2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-780ce8b5fbc9a25b602e Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001s-7290000000-19aa8376acd5d2a02e78 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]- 178.86798 predictedDeepCCS 1.0 (2019) [M+H]+ 181.29659 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.45775 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsDual specificity protein kinase CLK1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual specificity kinase acting on both serine/threonine and tyrosine-containing substrates. Phosphorylates serine- and arginine-rich (SR) proteins of the spliceosomal complex and may be a constituent of a network of regulatory mechanisms that enable SR proteins to control RNA splicing. Phosphorylates: SRSF1, SRSF3 and PTPN1 (PubMed:10480872, PubMed:19168442). Regulates the alternative splicing of tissue factor (F3) pre-mRNA in endothelial cells (PubMed:19168442)
- Specific Function
- ATP binding
- Gene Name
- CLK1
- Uniprot ID
- P49759
- Uniprot Name
- Dual specificity protein kinase CLK1
- Molecular Weight
- 57290.145 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual-specificity kinase which possesses both serine/threonine and tyrosine kinase activities (PubMed:20981014, PubMed:21127067, PubMed:23665168, PubMed:30773093, PubMed:8769099). Exhibits a substrate preference for proline at position P+1 and arginine at position P-3 (PubMed:23665168). Plays an important role in double-strand breaks (DSBs) repair following DNA damage (PubMed:31024071). Mechanistically, phosphorylates RNF169 and increases its ability to block accumulation of TP53BP1 at the DSB sites thereby promoting homologous recombination repair (HRR) (PubMed:30773093). Also acts as a positive regulator of transcription by acting as a CTD kinase that mediates phosphorylation of the CTD (C-terminal domain) of the large subunit of RNA polymerase II (RNAP II) POLR2A (PubMed:25620562, PubMed:29849146). May play a role in a signaling pathway regulating nuclear functions of cell proliferation (PubMed:14500717). Modulates alternative splicing by phosphorylating the splice factor SRSF6 (By similarity). Has pro-survival function and negatively regulates the apoptotic process (By similarity). Promotes cell survival upon genotoxic stress through phosphorylation of SIRT1 (By similarity). This in turn inhibits p53/TP53 activity and apoptosis (By similarity). Phosphorylates SEPTIN4, SEPTIN5 and SF3B1 at 'Thr-434' (By similarity)
- Specific Function
- actin binding
- Gene Name
- DYRK1A
- Uniprot ID
- Q13627
- Uniprot Name
- Dual specificity tyrosine-phosphorylation-regulated kinase 1A
- Molecular Weight
- 85583.41 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
3. DetailsDual specificity protein kinase CLK3
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Dual specificity kinase acting on both serine/threonine and tyrosine-containing substrates. Phosphorylates serine- and arginine-rich (SR) proteins of the spliceosomal complex. May be a constituent of a network of regulatory mechanisms that enable SR proteins to control RNA splicing and can cause redistribution of SR proteins from speckles to a diffuse nucleoplasmic distribution. Phosphorylates SRSF1 and SRSF3. Regulates the alternative splicing of tissue factor (F3) pre-mRNA in endothelial cells
- Specific Function
- ATP binding
- Gene Name
- CLK3
- Uniprot ID
- P49761
- Uniprot Name
- Dual specificity protein kinase CLK3
- Molecular Weight
- 58587.925 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 21:34 / Updated at August 26, 2024 19:21