N-(2-chloro-6-methylphenyl)-8-[(3S)-3-methylpiperazin-1-yl]imidazo[1,5-a]quinoxalin-4-amine
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Identification
- Generic Name
- N-(2-chloro-6-methylphenyl)-8-[(3S)-3-methylpiperazin-1-yl]imidazo[1,5-a]quinoxalin-4-amine
- DrugBank Accession Number
- DB08057
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 406.911
Monoisotopic: 406.167272473 - Chemical Formula
- C22H23ClN6
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTyrosine-protein kinase Lck 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 n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- N-arylpiperazines
- Alternative Parents
- Quinoxalines / Imidazo[1,5-a]pyrazines / Aniline and substituted anilines / Dialkylarylamines / Toluenes / Aminopyrazines / Chlorobenzenes / N-substituted imidazoles / Imidolactams / Aryl chlorides show 6 more
- Substituents
- Amine / Aminopyrazine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Chlorobenzene show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- VWJPPYCULHDHBB-HNNXBMFYSA-N
- InChI
- InChI=1S/C22H23ClN6/c1-14-4-3-5-17(23)21(14)27-22-20-11-24-13-29(20)19-10-16(6-7-18(19)26-22)28-9-8-25-15(2)12-28/h3-7,10-11,13,15,25H,8-9,12H2,1-2H3,(H,26,27)/t15-/m0/s1
- IUPAC Name
- N-(2-chloro-6-methylphenyl)-8-[(3S)-3-methylpiperazin-1-yl]imidazo[1,5-a]quinoxalin-4-amine
- SMILES
- [H][C@]1(C)CN(CCN1)C1=CC=C2N=C(NC3=C(C)C=CC=C3Cl)C3=CN=CN3C2=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 46937119
- PubChem Substance
- 99444528
- ChemSpider
- 25061091
- ZINC
- ZINC000039033598
- PDBe Ligand
- KSM
- PDB Entries
- 2zm4
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 0.00657 mg/mL ALOGPS logP 3.79 ALOGPS logP 3.74 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 14.32 Chemaxon pKa (Strongest Basic) 8.96 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.49 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 118.38 m3·mol-1 Chemaxon Polarizability 44.48 Å3 Chemaxon Number of Rings 5 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 + 0.8315 Caco-2 permeable - 0.5218 P-glycoprotein substrate Substrate 0.8437 P-glycoprotein inhibitor I Non-inhibitor 0.5098 P-glycoprotein inhibitor II Inhibitor 0.7332 Renal organic cation transporter Inhibitor 0.5996 CYP450 2C9 substrate Non-substrate 0.8071 CYP450 2D6 substrate Non-substrate 0.6414 CYP450 3A4 substrate Substrate 0.6246 CYP450 1A2 substrate Inhibitor 0.5686 CYP450 2C9 inhibitor Non-inhibitor 0.8617 CYP450 2D6 inhibitor Non-inhibitor 0.786 CYP450 2C19 inhibitor Non-inhibitor 0.6001 CYP450 3A4 inhibitor Inhibitor 0.6306 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6893 Ames test Non AMES toxic 0.7675 Carcinogenicity Non-carcinogens 0.8413 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7828 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7229 hERG inhibition (predictor II) Inhibitor 0.8608
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0000900000-ebc222527aa276dc6d40 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-053r-9000500000-dfdb515cd19fe3095ea1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0009700000-5813a37e8fba070ba669 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9000100000-e69a189a11c96798bb5c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0229-1009000000-53afc8b3a822a84b1730 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9004000000-0442bef1fd61098641e7 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]- 192.67891 predictedDeepCCS 1.0 (2019) [M+H]+ 195.03688 predictedDeepCCS 1.0 (2019) [M+Na]+ 201.29192 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsTyrosine-protein kinase Lck
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Non-receptor tyrosine-protein kinase that plays an essential role in the selection and maturation of developing T-cells in the thymus and in the function of mature T-cells. Plays a key role in T-cell antigen receptor (TCR)-linked signal transduction pathways. Constitutively associated with the cytoplasmic portions of the CD4 and CD8 surface receptors. Association of the TCR with a peptide antigen-bound MHC complex facilitates the interaction of CD4 and CD8 with MHC class II and class I molecules, respectively, thereby recruiting the associated LCK protein to the vicinity of the TCR/CD3 complex. LCK then phosphorylates tyrosine residues within the immunoreceptor tyrosine-based activation motifs (ITAM) of the cytoplasmic tails of the TCR-gamma chains and CD3 subunits, initiating the TCR/CD3 signaling pathway. Once stimulated, the TCR recruits the tyrosine kinase ZAP70, that becomes phosphorylated and activated by LCK. Following this, a large number of signaling molecules are recruited, ultimately leading to lymphokine production. LCK also contributes to signaling by other receptor molecules. Associates directly with the cytoplasmic tail of CD2, which leads to hyperphosphorylation and activation of LCK. Also plays a role in the IL2 receptor-linked signaling pathway that controls the T-cell proliferative response. Binding of IL2 to its receptor results in increased activity of LCK. Is expressed at all stages of thymocyte development and is required for the regulation of maturation events that are governed by both pre-TCR and mature alpha beta TCR. Phosphorylates other substrates including RUNX3, PTK2B/PYK2, the microtubule-associated protein MAPT, RHOH or TYROBP. Interacts with FYB2 (PubMed:27335501)
- Specific Function
- ATP binding
- Gene Name
- LCK
- Uniprot ID
- P06239
- Uniprot Name
- Tyrosine-protein kinase Lck
- Molecular Weight
- 58000.15 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 21:28 / Updated at June 12, 2020 16:52