(2S)-1-(Dimethylamino)-3-(4-{[4-(2-methylimidazo[1,2-a]pyridin-3-yl)-2-pyrimidinyl]amino}phenoxy)-2-propanol
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Identification
- Generic Name
- (2S)-1-(Dimethylamino)-3-(4-{[4-(2-methylimidazo[1,2-a]pyridin-3-yl)-2-pyrimidinyl]amino}phenoxy)-2-propanol
- DrugBank Accession Number
- DB07889
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (2S)-1-(Dimethylamino)-3-(4-{[4-(2-methylimidazo[1,2-a]pyridin-3-yl)-2-pyrimidinyl]amino}phenoxy)-2-propanol (DB07889)
- Weight
- Average: 418.4915
Monoisotopic: 418.211724106 - Chemical Formula
- C23H26N6O2
- 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 imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyridines
- Sub Class
- Not Available
- Direct Parent
- Imidazopyridines
- Alternative Parents
- Imidazo[1,2-a]pyridines / Aniline and substituted anilines / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Aminopyrimidines and derivatives / Pyridines and derivatives / N-substituted imidazoles / Heteroaromatic compounds / 1,2-aminoalcohols show 6 more
- Substituents
- 1,2-aminoalcohol / Alcohol / Alkyl aryl ether / Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- aminopyrimidine, imidazopyridine (CHEBI:42997)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- VCPXSBULBDYRLT-SFHVURJKSA-N
- InChI
- InChI=1S/C23H26N6O2/c1-16-22(29-13-5-4-6-21(29)25-16)20-11-12-24-23(27-20)26-17-7-9-19(10-8-17)31-15-18(30)14-28(2)3/h4-13,18,30H,14-15H2,1-3H3,(H,24,26,27)/t18-/m0/s1
- IUPAC Name
- (2S)-1-(dimethylamino)-3-{4-[(4-{2-methylimidazo[1,2-a]pyridin-3-yl}pyrimidin-2-yl)amino]phenoxy}propan-2-ol
- SMILES
- [H]N(C1=CC=C(OC[C@@H](O)CN(C)C)C=C1)C1=NC=CC(=N1)C1=C(C)N=C2C=CC=CN12
References
- General References
- Not Available
- External Links
- PubChem Compound
- 447653
- PubChem Substance
- 99444360
- ChemSpider
- 394684
- ZINC
- ZINC000002047516
- PDBe Ligand
- HDY
- PDB Entries
- 1oir
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 0.033 mg/mL ALOGPS logP 3.09 ALOGPS logP 2.27 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 13.8 Chemaxon pKa (Strongest Basic) 8.7 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 87.81 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 120.71 m3·mol-1 Chemaxon Polarizability 45.99 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 Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.7094 Caco-2 permeable + 0.5096 P-glycoprotein substrate Substrate 0.7481 P-glycoprotein inhibitor I Inhibitor 0.5524 P-glycoprotein inhibitor II Inhibitor 0.9402 Renal organic cation transporter Non-inhibitor 0.7855 CYP450 2C9 substrate Non-substrate 0.8496 CYP450 2D6 substrate Non-substrate 0.7898 CYP450 3A4 substrate Substrate 0.6386 CYP450 1A2 substrate Inhibitor 0.6632 CYP450 2C9 inhibitor Non-inhibitor 0.741 CYP450 2D6 inhibitor Inhibitor 0.6044 CYP450 2C19 inhibitor Non-inhibitor 0.7735 CYP450 3A4 inhibitor Non-inhibitor 0.6598 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5323 Ames test Non AMES toxic 0.5739 Carcinogenicity Non-carcinogens 0.8516 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.4507 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7836 hERG inhibition (predictor II) Inhibitor 0.582
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-2000900000-00738e7f9d46df40e1da Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009200000-fbeea70c9adb2a84e491 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0k96-2009500000-4531f8864d13bc2d4ebf Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0cdi-9005100000-e31b2b4af72ae3cc0408 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-4109300000-c5154dd8406fd9421399 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0119000000-0deba2d2089393eeca46 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]- 193.92772 predictedDeepCCS 1.0 (2019) [M+H]+ 196.32326 predictedDeepCCS 1.0 (2019) [M+Na]+ 202.2885 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 21:26 / Updated at June 12, 2020 16:52