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Identification
- Generic Name
- 3-methyl-N-(pyridin-4-ylmethyl)imidazo[1,2-a]pyrazin-8-amine
- DrugBank Accession Number
- DB08533
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 3-methyl-N-(pyridin-4-ylmethyl)imidazo[1,2-a]pyrazin-8-amine (DB08533)
- Weight
- Average: 239.2758
Monoisotopic: 239.117095441 - Chemical Formula
- C13H13N5
- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
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 imidazopyrazines. These are organic heteropolycyclic compounds containing a pyrazine ring fused to an imidazole ring. These also include hydrogenated derivatives of the imidazopyrazine moiety. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyrazine is a 6-membered ring consisting of six carbon atoms and two nitrogen centers at ring positions 1 and 4.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrazines
- Sub Class
- Not Available
- Direct Parent
- Imidazopyrazines
- Alternative Parents
- Secondary alkylarylamines / Aminopyrazines / Pyridines and derivatives / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aminopyrazine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidazopyrazine / Imidolactam
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- LXRVAGIYXNQOKP-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H13N5/c1-10-8-17-13-12(15-6-7-18(10)13)16-9-11-2-4-14-5-3-11/h2-8H,9H2,1H3,(H,15,16)
- IUPAC Name
- 3-methyl-N-[(pyridin-4-yl)methyl]imidazo[1,2-a]pyrazin-8-amine
- SMILES
- CC1=CN=C2N1C=CN=C2NCC1=CC=NC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 9991833
- PubChem Substance
- 99445004
- ChemSpider
- 8167415
- ZINC
- ZINC000003820150
- PDBe Ligand
- SCE
- PDB Entries
- 2r3h
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 0.0432 mg/mL ALOGPS logP 1.43 ALOGPS logP 0.32 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 16.06 Chemaxon pKa (Strongest Basic) 5.09 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 55.11 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 71.89 m3·mol-1 Chemaxon Polarizability 25.85 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9932 Blood Brain Barrier + 0.9757 Caco-2 permeable + 0.5633 P-glycoprotein substrate Non-substrate 0.5671 P-glycoprotein inhibitor I Non-inhibitor 0.8525 P-glycoprotein inhibitor II Inhibitor 0.6921 Renal organic cation transporter Non-inhibitor 0.5423 CYP450 2C9 substrate Non-substrate 0.8039 CYP450 2D6 substrate Non-substrate 0.8204 CYP450 3A4 substrate Non-substrate 0.6579 CYP450 1A2 substrate Inhibitor 0.9528 CYP450 2C9 inhibitor Non-inhibitor 0.9233 CYP450 2D6 inhibitor Inhibitor 0.7061 CYP450 2C19 inhibitor Inhibitor 0.6774 CYP450 3A4 inhibitor Non-inhibitor 0.5982 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8834 Ames test AMES toxic 0.889 Carcinogenicity Non-carcinogens 0.8749 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5815 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8166 hERG inhibition (predictor II) Non-inhibitor 0.6186
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-06r6-6940000000-7db70fa5402c32ee2a15 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-1090000000-98d55008a4960b7f4953 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0019-0690000000-319a0549cc6344abd98d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-1900000000-b2c00554f3b4390cf7cf Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-ebfccaa261e456a603fe Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03e9-5940000000-0517406ab0b68db85ff5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0563-9300000000-327baac4bfe791d40eb8 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]- 146.1292 predictedDeepCCS 1.0 (2019) [M+H]+ 148.52477 predictedDeepCCS 1.0 (2019) [M+Na]+ 154.48099 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 21:32 / Updated at June 12, 2020 16:52