(2R)-1-[4-({4-[(2,5-Dichlorophenyl)amino]-2-pyrimidinyl}amino)phenoxy]-3-(dimethylamino)-2-propanol
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Identification
- Generic Name
- (2R)-1-[4-({4-[(2,5-Dichlorophenyl)amino]-2-pyrimidinyl}amino)phenoxy]-3-(dimethylamino)-2-propanol
- DrugBank Accession Number
- DB07750
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (2R)-1-[4-({4-[(2,5-Dichlorophenyl)amino]-2-pyrimidinyl}amino)phenoxy]-3-(dimethylamino)-2-propanol (DB07750)
- Weight
- Average: 448.346
Monoisotopic: 447.122880419 - Chemical Formula
- C21H23Cl2N5O2
- 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 dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Halobenzenes
- Direct Parent
- Dichlorobenzenes
- Alternative Parents
- Aniline and substituted anilines / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Aminopyrimidines and derivatives / Aryl chlorides / Imidolactams / Heteroaromatic compounds / Trialkylamines / 1,2-aminoalcohols show 6 more
- Substituents
- 1,2-aminoalcohol / 1,4-dichlorobenzene / Alcohol / Alkyl aryl ether / Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide show 20 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- aminopyrimidine, dichlorobenzene (CHEBI:47405)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- GNLAGGCSJGJECE-MRXNPFEDSA-N
- InChI
- InChI=1S/C21H23Cl2N5O2/c1-28(2)12-16(29)13-30-17-6-4-15(5-7-17)25-21-24-10-9-20(27-21)26-19-11-14(22)3-8-18(19)23/h3-11,16,29H,12-13H2,1-2H3,(H2,24,25,26,27)/t16-/m1/s1
- IUPAC Name
- (2R)-1-[4-({4-[(2,5-dichlorophenyl)amino]pyrimidin-2-yl}amino)phenoxy]-3-(dimethylamino)propan-2-ol
- SMILES
- [H]N(C1=CC=C(OC[C@H](O)CN(C)C)C=C1)C1=NC=CC(=N1)N([H])C1=C(Cl)C=CC(Cl)=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 445952
- PubChem Substance
- 99444221
- ChemSpider
- 393432
- ZINC
- ZINC000000602494
- PDBe Ligand
- FAL
- PDB Entries
- 1h01
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 0.02 mg/mL ALOGPS logP 4.38 ALOGPS logP 4.64 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 13.76 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 120.01 m3·mol-1 Chemaxon Polarizability 47.26 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 + 0.9689 Blood Brain Barrier - 0.5075 Caco-2 permeable + 0.522 P-glycoprotein substrate Substrate 0.6666 P-glycoprotein inhibitor I Non-inhibitor 0.7073 P-glycoprotein inhibitor II Inhibitor 0.9174 Renal organic cation transporter Non-inhibitor 0.7376 CYP450 2C9 substrate Non-substrate 0.823 CYP450 2D6 substrate Non-substrate 0.793 CYP450 3A4 substrate Substrate 0.5622 CYP450 1A2 substrate Non-inhibitor 0.5124 CYP450 2C9 inhibitor Non-inhibitor 0.774 CYP450 2D6 inhibitor Non-inhibitor 0.5488 CYP450 2C19 inhibitor Non-inhibitor 0.6217 CYP450 3A4 inhibitor Non-inhibitor 0.6943 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5917 Ames test Non AMES toxic 0.6503 Carcinogenicity Non-carcinogens 0.8644 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3546 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.74 hERG inhibition (predictor II) Inhibitor 0.5861
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0000900000-e4130d5f5ec90294ede5 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-002k-1118900000-62b191693c62e463f95f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-008i-0009400000-cd65157d4c54f72b0676 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000y-9103300000-82656514aa9770f44497 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08fr-9003100000-b9574ba46d29bed074eb Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9004100000-d011dc9b61bb6d7f4309 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]- 193.83376 predictedDeepCCS 1.0 (2019) [M+H]+ 196.19176 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.3846 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