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Identification
- Generic Name
- 4-{[(2-Oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]amino}-N-(1,3-thiazol-2-yl)benzenesulfonamide
- DrugBank Accession Number
- DB08125
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 4-{[(2-Oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]amino}-N-(1,3-thiazol-2-yl)benzenesulfonamide (DB08125)
- Weight
- Average: 398.459
Monoisotopic: 398.050731714 - Chemical Formula
- C18H14N4O3S2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UCyclin-dependent kinase 2 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
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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 aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonamides
- Direct Parent
- Aminobenzenesulfonamides
- Alternative Parents
- Benzenesulfonyl compounds / Indolines / Aniline and substituted anilines / Secondary alkylarylamines / Organosulfonamides / Aminosulfonyl compounds / Heteroaromatic compounds / Thiazoles / Vinylogous amides / Secondary carboxylic acid amides show 8 more
- Substituents
- Amine / Amino acid or derivatives / Aminobenzenesulfonamide / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenesulfonyl group / Carbonyl group show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- sulfonamide, 1,3-thiazole, oxindole (CHEBI:43762)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- BOMPRXSVSIPRDT-PTNGSMBKSA-N
- InChI
- InChI=1S/C18H14N4O3S2/c23-17-15(14-3-1-2-4-16(14)21-17)11-20-12-5-7-13(8-6-12)27(24,25)22-18-19-9-10-26-18/h1-11,20H,(H,19,22)(H,21,23)/b15-11-
- IUPAC Name
- 4-({[(3Z)-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}amino)-N-(1,3-thiazol-2-yl)benzene-1-sulfonamide
- SMILES
- O=C1NC2=CC=CC=C2\C1=C\NC1=CC=C(C=C1)S(=O)(=O)NC1=NC=CS1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5288711
- PubChem Substance
- 99444596
- ChemSpider
- 4450815
- ChEMBL
- CHEMBL1234088
- ZINC
- ZINC000010254751
- PDBe Ligand
- LS4
- PDB Entries
- 1ke8
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 0.0108 mg/mL ALOGPS logP 2.9 ALOGPS logP 2.34 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 6.9 Chemaxon pKa (Strongest Basic) 0.59 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 100.19 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 105.44 m3·mol-1 Chemaxon Polarizability 39.85 Å3 Chemaxon Number of Rings 4 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 + 0.9426 Blood Brain Barrier - 0.6586 Caco-2 permeable - 0.595 P-glycoprotein substrate Non-substrate 0.7332 P-glycoprotein inhibitor I Non-inhibitor 0.6949 P-glycoprotein inhibitor II Inhibitor 0.5 Renal organic cation transporter Non-inhibitor 0.8647 CYP450 2C9 substrate Non-substrate 0.5701 CYP450 2D6 substrate Non-substrate 0.855 CYP450 3A4 substrate Non-substrate 0.684 CYP450 1A2 substrate Non-inhibitor 0.7436 CYP450 2C9 inhibitor Non-inhibitor 0.585 CYP450 2D6 inhibitor Non-inhibitor 0.8783 CYP450 2C19 inhibitor Non-inhibitor 0.6592 CYP450 3A4 inhibitor Inhibitor 0.5439 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9128 Ames test Non AMES toxic 0.7462 Carcinogenicity Non-carcinogens 0.8082 Biodegradation Not ready biodegradable 0.9859 Rat acute toxicity 2.4649 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.974 hERG inhibition (predictor II) Non-inhibitor 0.8305
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0095000000-cd9108c34f72a010d0eb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-795eb6a4ce2c664044f8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-25fdb282aded89a88adc Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-053u-1972000000-1a5282fddf3d3d92b6f2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00kk-2029000000-91650b0d0edd5982f35a Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00kf-5693000000-62f7439d232f7b9c8971 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]- 185.26007 predictedDeepCCS 1.0 (2019) [M+H]+ 187.74266 predictedDeepCCS 1.0 (2019) [M+Na]+ 194.90382 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Serine/threonine-protein kinase involved in the control of the cell cycle; essential for meiosis, but dispensable for mitosis (PubMed:10499802, PubMed:10884347, PubMed:10995386, PubMed:10995387, PubMed:11051553, PubMed:11113184, PubMed:12944431, PubMed:15800615, PubMed:17495531, PubMed:19966300, PubMed:20935635, PubMed:21262353, PubMed:21596315, PubMed:28216226, PubMed:28666995). Phosphorylates CABLES1, CTNNB1, CDK2AP2, ERCC6, NBN, USP37, p53/TP53, NPM1, CDK7, RB1, BRCA2, MYC, NPAT, EZH2 (PubMed:10499802, PubMed:10995386, PubMed:10995387, PubMed:11051553, PubMed:11113184, PubMed:12944431, PubMed:15800615, PubMed:19966300, PubMed:20935635, PubMed:21262353, PubMed:21596315, PubMed:28216226). Triggers duplication of centrosomes and DNA (PubMed:11051553). Acts at the G1-S transition to promote the E2F transcriptional program and the initiation of DNA synthesis, and modulates G2 progression; controls the timing of entry into mitosis/meiosis by controlling the subsequent activation of cyclin B/CDK1 by phosphorylation, and coordinates the activation of cyclin B/CDK1 at the centrosome and in the nucleus (PubMed:18372919, PubMed:19238148, PubMed:19561645). Crucial role in orchestrating a fine balance between cellular proliferation, cell death, and DNA repair in embryonic stem cells (ESCs) (PubMed:18372919, PubMed:19238148, PubMed:19561645). Activity of CDK2 is maximal during S phase and G2; activated by interaction with cyclin E during the early stages of DNA synthesis to permit G1-S transition, and subsequently activated by cyclin A2 (cyclin A1 in germ cells) during the late stages of DNA replication to drive the transition from S phase to mitosis, the G2 phase (PubMed:18372919, PubMed:19238148, PubMed:19561645). EZH2 phosphorylation promotes H3K27me3 maintenance and epigenetic gene silencing (PubMed:20935635). Cyclin E/CDK2 prevents oxidative stress-mediated Ras-induced senescence by phosphorylating MYC (PubMed:19966300). Involved in G1-S phase DNA damage checkpoint that prevents cells with damaged DNA from initiating mitosis; regulates homologous recombination-dependent repair by phosphorylating BRCA2, this phosphorylation is low in S phase when recombination is active, but increases as cells progress towards mitosis (PubMed:15800615, PubMed:20195506, PubMed:21319273). In response to DNA damage, double-strand break repair by homologous recombination a reduction of CDK2-mediated BRCA2 phosphorylation (PubMed:15800615). Involoved in regulation of telomere repar by mediating phosphorylation of NBN (PubMed:28216226). Phosphorylation of RB1 disturbs its interaction with E2F1 (PubMed:10499802). NPM1 phosphorylation by cyclin E/CDK2 promotes its dissociates from unduplicated centrosomes, thus initiating centrosome duplication (PubMed:11051553). Cyclin E/CDK2-mediated phosphorylation of NPAT at G1-S transition and until prophase stimulates the NPAT-mediated activation of histone gene transcription during S phase (PubMed:10995386, PubMed:10995387). Required for vitamin D-mediated growth inhibition by being itself inactivated (PubMed:20147522). Involved in the nitric oxide- (NO) mediated signaling in a nitrosylation/activation-dependent manner (PubMed:20079829). USP37 is activated by phosphorylation and thus triggers G1-S transition (PubMed:21596315). CTNNB1 phosphorylation regulates insulin internalization (PubMed:21262353). Phosphorylates FOXP3 and negatively regulates its transcriptional activity and protein stability (By similarity). Phosphorylates ERCC6 which is essential for its chromatin remodeling activity at DNA double-strand breaks (PubMed:29203878)
- Specific Function
- Atp binding
- Gene Name
- CDK2
- Uniprot ID
- P24941
- Uniprot Name
- Cyclin-dependent kinase 2
- Molecular Weight
- 33929.215 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 21:28 / Updated at June 12, 2020 16:52