6-(3,4-DIHYDROXYBENZYL)-3-ETHYL-1-(2,4,6-TRICHLOROPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- 6-(3,4-DIHYDROXYBENZYL)-3-ETHYL-1-(2,4,6-TRICHLOROPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE
- DrugBank Accession Number
- DB07606
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 6-(3,4-DIHYDROXYBENZYL)-3-ETHYL-1-(2,4,6-TRICHLOROPHENYL)-1H-PYRAZOLO[3,4-D]PYRIMIDIN-4(5H)-ONE (DB07606)
- Weight
- Average: 465.717
Monoisotopic: 464.020973487 - Chemical Formula
- C20H15Cl3N4O3
- 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 phenylpyrazoles. These are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Azoles
- Sub Class
- Pyrazoles
- Direct Parent
- Phenylpyrazoles
- Alternative Parents
- Pyrazolo[3,4-d]pyrimidines / Catechols / Pyrimidones / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Chlorobenzenes / Aryl chlorides / Vinylogous amides / Heteroaromatic compounds / Lactams show 7 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Catechol / Chlorobenzene / Halobenzene show 19 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- trichlorobenzene, pyrazolopyrimidine (CHEBI:47364)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- OPRAIFVPXXVXDL-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H15Cl3N4O3/c1-2-13-17-19(27(26-13)18-11(22)7-10(21)8-12(18)23)24-16(25-20(17)30)6-9-3-4-14(28)15(29)5-9/h3-5,7-8,28-29H,2,6H2,1H3,(H,24,25,30)
- IUPAC Name
- 6-[(3,4-dihydroxyphenyl)methyl]-3-ethyl-1-(2,4,6-trichlorophenyl)-1H,4H,5H-pyrazolo[3,4-d]pyrimidin-4-one
- SMILES
- CCC1=NN(C2=C1C(=O)NC(CC1=CC(O)=C(O)C=C1)=N2)C1=C(Cl)C=C(Cl)C=C1Cl
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5327057
- PubChem Substance
- 99444077
- ChemSpider
- 20120282
- BindingDB
- 6021
- ChEMBL
- CHEMBL425181
- ZINC
- ZINC000013585203
- PDBe Ligand
- D05
- PDB Entries
- 2b54
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 0.0173 mg/mL ALOGPS logP 5.31 ALOGPS logP 4.82 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 8.87 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 99.74 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 117.32 m3·mol-1 Chemaxon Polarizability 44.12 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 + 1.0 Blood Brain Barrier + 0.7089 Caco-2 permeable - 0.6243 P-glycoprotein substrate Substrate 0.5973 P-glycoprotein inhibitor I Non-inhibitor 0.8393 P-glycoprotein inhibitor II Non-inhibitor 0.7895 Renal organic cation transporter Non-inhibitor 0.9007 CYP450 2C9 substrate Non-substrate 0.709 CYP450 2D6 substrate Non-substrate 0.8245 CYP450 3A4 substrate Substrate 0.6345 CYP450 1A2 substrate Non-inhibitor 0.6779 CYP450 2C9 inhibitor Inhibitor 0.5738 CYP450 2D6 inhibitor Non-inhibitor 0.8205 CYP450 2C19 inhibitor Non-inhibitor 0.6236 CYP450 3A4 inhibitor Non-inhibitor 0.7322 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8514 Ames test Non AMES toxic 0.5877 Carcinogenicity Non-carcinogens 0.7061 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4524 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9756 hERG inhibition (predictor II) Non-inhibitor 0.7449
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0000900000-90c00aef899b6b2ed643 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0000900000-0f2003b49c689081c22d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03e9-0000900000-aa244a4e503834a19f90 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0000900000-0bbceb643142294c01f3 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-016s-0002900000-01da35638b87a0173bff Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9100200000-571aee9aed123c854cb7 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]- 194.34096 predictedDeepCCS 1.0 (2019) [M+H]+ 196.73654 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.64906 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