N-(2-chlorophenyl)-5-phenylimidazo[1,5-a]pyrazin-8-amine
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Identification
- Generic Name
- N-(2-chlorophenyl)-5-phenylimidazo[1,5-a]pyrazin-8-amine
- DrugBank Accession Number
- DB08055
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 320.776
Monoisotopic: 320.082874143 - Chemical Formula
- C18H13ClN4
- 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
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- 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 imidazo[1,5-a]pyrazines. These are aromatic heteropolycyclic compounds containing an imidazole ring fused to and sharing one nitrogen with a pyrazine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazo[1,5-a]pyrazines
- Sub Class
- Not Available
- Direct Parent
- Imidazo[1,5-a]pyrazines
- Alternative Parents
- Aniline and substituted anilines / Chlorobenzenes / Aminopyrazines / N-substituted imidazoles / Imidolactams / Aryl chlorides / Heteroaromatic compounds / Secondary amines / Azacyclic compounds / Organopnictogen compounds show 2 more
- Substituents
- Amine / Aminopyrazine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzenoid / Chlorobenzene show 15 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
- NNBICZMPIJMWGC-UHFFFAOYSA-N
- InChI
- InChI=1S/C18H13ClN4/c19-14-8-4-5-9-15(14)22-18-17-10-20-12-23(17)16(11-21-18)13-6-2-1-3-7-13/h1-12H,(H,21,22)
- IUPAC Name
- N-(2-chlorophenyl)-5-phenylimidazo[1,5-a]pyrazin-8-amine
- SMILES
- ClC1=C(NC2=NC=C(N3C=NC=C23)C2=CC=CC=C2)C=CC=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 44563262
- PubChem Substance
- 99444526
- ChemSpider
- 23332732
- BindingDB
- 50246553
- ChEMBL
- CHEMBL462228
- ZINC
- ZINC000039033939
- PDBe Ligand
- KSF
- PDB Entries
- 2zm1
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 0.00342 mg/mL ALOGPS logP 3.89 ALOGPS logP 3.4 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 13.77 Chemaxon pKa (Strongest Basic) 6.33 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 42.22 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 92.8 m3·mol-1 Chemaxon Polarizability 33.52 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9968 Blood Brain Barrier + 0.9264 Caco-2 permeable + 0.7341 P-glycoprotein substrate Non-substrate 0.7545 P-glycoprotein inhibitor I Non-inhibitor 0.7463 P-glycoprotein inhibitor II Inhibitor 0.7788 Renal organic cation transporter Non-inhibitor 0.7095 CYP450 2C9 substrate Non-substrate 0.8323 CYP450 2D6 substrate Non-substrate 0.9098 CYP450 3A4 substrate Non-substrate 0.5507 CYP450 1A2 substrate Inhibitor 0.914 CYP450 2C9 inhibitor Non-inhibitor 0.6943 CYP450 2D6 inhibitor Inhibitor 0.6579 CYP450 2C19 inhibitor Inhibitor 0.9013 CYP450 3A4 inhibitor Inhibitor 0.7573 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9607 Ames test AMES toxic 0.7171 Carcinogenicity Non-carcinogens 0.8594 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5290 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9461 hERG inhibition (predictor II) Non-inhibitor 0.5975
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-014l-1951000000-7d403cbfe887b0933aac Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009000000-7e727767c1aa4988afdd Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0009000000-96d1bc3865d73936bfb2 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0009000000-ec0f8365ec1ac462fcdd Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0119000000-47feeeeb152b08c6e749 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-1000-1790000000-4c03e173f63fc5b311aa Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0gc0-2789000000-ed040ddb4b8e232734ec 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]- 170.2286 predictedDeepCCS 1.0 (2019) [M+H]+ 172.58661 predictedDeepCCS 1.0 (2019) [M+Na]+ 179.33333 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