1-(3-(2,4-DIMETHYLTHIAZOL-5-YL)-4-OXO-2,4-DIHYDROINDENO[1,2-C]PYRAZOL-5-YL)-3-(4-METHYLPIPERAZIN-1-YL)UREA
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Identification
- Generic Name
- 1-(3-(2,4-DIMETHYLTHIAZOL-5-YL)-4-OXO-2,4-DIHYDROINDENO[1,2-C]PYRAZOL-5-YL)-3-(4-METHYLPIPERAZIN-1-YL)UREA
- DrugBank Accession Number
- DB07622
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 1-(3-(2,4-DIMETHYLTHIAZOL-5-YL)-4-OXO-2,4-DIHYDROINDENO[1,2-C]PYRAZOL-5-YL)-3-(4-METHYLPIPERAZIN-1-YL)UREA (DB07622)
- Weight
- Average: 437.518
Monoisotopic: 437.163393705 - Chemical Formula
- C21H23N7O2S
- 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 2,4,5-trisubstituted thiazoles. These are compounds containing a thiazole ring substituted at positions 2, 4 and 5 only.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Thiazoles
- Direct Parent
- 2,4,5-trisubstituted thiazoles
- Alternative Parents
- Aryl ketones / N-methylpiperazines / Benzenoids / Vinylogous amides / Semicarbazides / Pyrazoles / Heteroaromatic compounds / Trialkylamines / Organic carbonic acids and derivatives / Azacyclic compounds show 3 more
- Substituents
- 1,4-diazinane / 2,4,5-trisubstituted 1,3-thiazole / Amine / Aromatic heteropolycyclic compound / Aryl ketone / Azacycle / Benzenoid / Carbonic acid derivative / Carbonyl group / Heteroaromatic compound show 16 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 1,3-thiazole, N-methylpiperazine, indenopyrazole (CHEBI:41766)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- KRKQVGZXTNLQSV-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H23N7O2S/c1-11-20(31-12(2)22-11)18-16-17(24-25-18)13-5-4-6-14(15(13)19(16)29)23-21(30)26-28-9-7-27(3)8-10-28/h4-6H,7-10H2,1-3H3,(H,24,25)(H2,23,26,30)
- IUPAC Name
- 3-[3-(2,4-dimethyl-1,3-thiazol-5-yl)-4-oxo-2H,4H-indeno[1,2-c]pyrazol-5-yl]-1-(4-methylpiperazin-1-yl)urea
- SMILES
- CN1CCN(CC1)NC(=O)NC1=CC=CC2=C1C(=O)C1=C(NN=C21)C1=C(C)N=C(C)S1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5288018
- PubChem Substance
- 99444093
- ChemSpider
- 4450263
- BindingDB
- 6051
- ChEMBL
- CHEMBL325023
- ZINC
- ZINC000000595002
- PDBe Ligand
- D42
- PDB Entries
- 2b52
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 0.0303 mg/mL ALOGPS logP 2.06 ALOGPS logP 1.44 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 8.74 Chemaxon pKa (Strongest Basic) 6.85 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 106.25 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 120.75 m3·mol-1 Chemaxon Polarizability 46.71 Å3 Chemaxon Number of Rings 5 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 + 0.9883 Blood Brain Barrier + 0.7377 Caco-2 permeable - 0.596 P-glycoprotein substrate Substrate 0.8236 P-glycoprotein inhibitor I Inhibitor 0.752 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.7413 CYP450 2C9 substrate Non-substrate 0.6423 CYP450 2D6 substrate Non-substrate 0.7509 CYP450 3A4 substrate Substrate 0.6733 CYP450 1A2 substrate Non-inhibitor 0.7791 CYP450 2C9 inhibitor Inhibitor 0.5 CYP450 2D6 inhibitor Non-inhibitor 0.847 CYP450 2C19 inhibitor Non-inhibitor 0.5788 CYP450 3A4 inhibitor Non-inhibitor 0.6311 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5059 Ames test AMES toxic 0.519 Carcinogenicity Non-carcinogens 0.8448 Biodegradation Not ready biodegradable 0.9939 Rat acute toxicity 2.6117 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5718 hERG inhibition (predictor II) Inhibitor 0.8567
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0000900000-8bf5bc196b3afcb611b5 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-1201900000-adb2c7e985a0a99505b8 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000b-0180900000-34ed4179516a2574804c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000t-9334300000-3a810e92813ec37c3b13 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9401100000-40e7ff606cdeea901de5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0aba-2029200000-ab80186abd5b2c8f290f 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]- 201.91396 predictedDeepCCS 1.0 (2019) [M+H]+ 204.27196 predictedDeepCCS 1.0 (2019) [M+Na]+ 211.36215 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 21:24 / Updated at June 12, 2020 16:52