(2S)-1-[4-({6-[(2,6-Difluorophenyl)amino]-4-pyrimidinyl}amino)phenoxy]-3-(dimethylamino)-2-propanol
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Identification
- Generic Name
- (2S)-1-[4-({6-[(2,6-Difluorophenyl)amino]-4-pyrimidinyl}amino)phenoxy]-3-(dimethylamino)-2-propanol
- DrugBank Accession Number
- DB07751
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (2S)-1-[4-({6-[(2,6-Difluorophenyl)amino]-4-pyrimidinyl}amino)phenoxy]-3-(dimethylamino)-2-propanol (DB07751)
- Weight
- Average: 415.4364
Monoisotopic: 415.181981415 - Chemical Formula
- C21H23F2N5O2
- 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 phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Aniline and substituted anilines / Phenoxy compounds / Alkyl aryl ethers / Aminopyrimidines and derivatives / Fluorobenzenes / Aryl fluorides / Imidolactams / Heteroaromatic compounds / 1,2-aminoalcohols / Secondary alcohols show 6 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle show 22 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- organofluorine compound, aminopyrimidine (CHEBI:42543)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- ZVSBKYYVBCKDBO-HNNXBMFYSA-N
- InChI
- InChI=1S/C21H23F2N5O2/c1-28(2)11-15(29)12-30-16-8-6-14(7-9-16)26-19-10-20(25-13-24-19)27-21-17(22)4-3-5-18(21)23/h3-10,13,15,29H,11-12H2,1-2H3,(H2,24,25,26,27)/t15-/m0/s1
- IUPAC Name
- (2S)-1-[4-({6-[(2,6-difluorophenyl)amino]pyrimidin-4-yl}amino)phenoxy]-3-(dimethylamino)propan-2-ol
- SMILES
- [H]N(C1=CC=C(OC[C@@H](O)CN(C)C)C=C1)C1=CC(=NC=N1)N([H])C1=C(F)C=CC=C1F
References
- General References
- Not Available
- External Links
- PubChem Compound
- 445950
- PubChem Substance
- 99444222
- ChemSpider
- 393430
- ZINC
- ZINC000003581447
- PDBe Ligand
- FAP
- PDB Entries
- 1h00
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 0.036 mg/mL ALOGPS logP 3.45 ALOGPS logP 3.63 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 12.42 Chemaxon pKa (Strongest Basic) 8.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 82.54 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 111.2 m3·mol-1 Chemaxon Polarizability 42.79 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 Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8404 Blood Brain Barrier + 0.5973 Caco-2 permeable + 0.5233 P-glycoprotein substrate Substrate 0.686 P-glycoprotein inhibitor I Non-inhibitor 0.6029 P-glycoprotein inhibitor II Inhibitor 0.9207 Renal organic cation transporter Non-inhibitor 0.7848 CYP450 2C9 substrate Non-substrate 0.8242 CYP450 2D6 substrate Non-substrate 0.7824 CYP450 3A4 substrate Substrate 0.5201 CYP450 1A2 substrate Non-inhibitor 0.5085 CYP450 2C9 inhibitor Non-inhibitor 0.7862 CYP450 2D6 inhibitor Inhibitor 0.6151 CYP450 2C19 inhibitor Non-inhibitor 0.5626 CYP450 3A4 inhibitor Non-inhibitor 0.6863 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7241 Ames test Non AMES toxic 0.6329 Carcinogenicity Non-carcinogens 0.8637 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4006 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9285 hERG inhibition (predictor II) Inhibitor 0.7274
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-0001900000-3088efd247ebdde2540b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0537-3009000000-2d47c4ee46539cb50654 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0119200000-b096781c1591f68e4974 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08fr-9002000000-c1f1d9b03a2bee60886a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9143000000-7befae45e180c26122f9 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0459000000-88f4c1dc6c9a978d5976 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]- 190.68913 predictedDeepCCS 1.0 (2019) [M+H]+ 193.04715 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.14027 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 21:25 / Updated at June 12, 2020 16:52