N~2~-1H-benzimidazol-5-yl-N~4~-(3-cyclopropyl-1H-pyrazol-5-yl)pyrimidine-2,4-diamine
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Identification
- Generic Name
- N~2~-1H-benzimidazol-5-yl-N~4~-(3-cyclopropyl-1H-pyrazol-5-yl)pyrimidine-2,4-diamine
- DrugBank Accession Number
- DB07382
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 332.3625
Monoisotopic: 332.149792552 - Chemical Formula
- C17H16N8
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ASerine/threonine-protein kinase/endoribonuclease IRE1 inhibitorHumans - 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 benzimidazoles. These are organic compounds containing a benzene ring fused to an imidazole ring (five member ring containing a nitrogen atom, 4 carbon atoms, and two double bonds).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzimidazoles
- Sub Class
- Not Available
- Direct Parent
- Benzimidazoles
- Alternative Parents
- Aminopyrimidines and derivatives / Imidolactams / Benzenoids / Pyrazoles / Imidazoles / Heteroaromatic compounds / Secondary amines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzimidazole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- WJNBSTLIALIIEW-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H16N8/c1-2-10(1)13-8-16(25-24-13)22-15-5-6-18-17(23-15)21-11-3-4-12-14(7-11)20-9-19-12/h3-10H,1-2H2,(H,19,20)(H3,18,21,22,23,24,25)
- IUPAC Name
- N2-(1H-1,3-benzodiazol-5-yl)-N4-(3-cyclopropyl-1H-pyrazol-5-yl)pyrimidine-2,4-diamine
- SMILES
- C1CC1C1=NNC(NC2=CC=NC(NC3=CC4=C(NC=N4)C=C3)=N2)=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 42627755
- PubChem Substance
- 99443853
- ChemSpider
- 25057507
- ZINC
- ZINC000040163635
- PDBe Ligand
- APJ
- PDB Entries
- 3fbv / 3sdj
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 0.0213 mg/mL ALOGPS logP 3.43 ALOGPS logP 2.79 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 12.38 Chemaxon pKa (Strongest Basic) 6.68 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 107.2 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 93.8 m3·mol-1 Chemaxon Polarizability 35.98 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 + 0.9969 Blood Brain Barrier + 0.9155 Caco-2 permeable + 0.5229 P-glycoprotein substrate Non-substrate 0.6155 P-glycoprotein inhibitor I Non-inhibitor 0.8519 P-glycoprotein inhibitor II Non-inhibitor 0.6675 Renal organic cation transporter Non-inhibitor 0.7158 CYP450 2C9 substrate Non-substrate 0.8151 CYP450 2D6 substrate Non-substrate 0.8424 CYP450 3A4 substrate Non-substrate 0.6845 CYP450 1A2 substrate Inhibitor 0.8205 CYP450 2C9 inhibitor Non-inhibitor 0.7232 CYP450 2D6 inhibitor Non-inhibitor 0.8296 CYP450 2C19 inhibitor Non-inhibitor 0.6683 CYP450 3A4 inhibitor Inhibitor 0.6613 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6972 Ames test Non AMES toxic 0.6509 Carcinogenicity Non-carcinogens 0.9009 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5022 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8739 hERG inhibition (predictor II) Non-inhibitor 0.8058
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-416b3c94a1e482722da1 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-47600d1f1bcd3c7fc1e3 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-d307db1f3c07c712557c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-02tc-0296000000-a3a325ab5631878bc4bb Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0039000000-f5f042b60027eaaf4071 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-053r-1911000000-bbff16ef8f84754c34bc 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]- 186.4447 predictedDeepCCS 1.0 (2019) [M+H]+ 188.82185 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.25545 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine/threonine-protein kinase and endoribonuclease that acts as a key sensor for the endoplasmic reticulum unfolded protein response (UPR) (PubMed:11175748, PubMed:11779464, PubMed:12637535, PubMed:21317875, PubMed:28128204, PubMed:30118681, PubMed:9637683). In unstressed cells, the endoplasmic reticulum luminal domain is maintained in its inactive monomeric state by binding to the endoplasmic reticulum chaperone HSPA5/BiP (PubMed:21317875). Accumulation of misfolded proteins in the endoplasmic reticulum causes release of HSPA5/BiP, allowing the luminal domain to homodimerize, promoting autophosphorylation of the kinase domain and subsequent activation of the endoribonuclease activity (PubMed:21317875). The endoribonuclease activity is specific for XBP1 mRNA and excises 26 nucleotides from XBP1 mRNA (PubMed:11779464, PubMed:21317875, PubMed:24508390). The resulting spliced transcript of XBP1 encodes a transcriptional activator protein that up-regulates expression of UPR target genes (PubMed:11779464, PubMed:21317875, PubMed:24508390). Acts as an upstream signal for ER stress-induced GORASP2-mediated unconventional (ER/Golgi-independent) trafficking of CFTR to cell membrane by modulating the expression and localization of SEC16A (PubMed:21884936, PubMed:28067262)
- Specific Function
- ADP binding
- Gene Name
- ERN1
- Uniprot ID
- O75460
- Uniprot Name
- Serine/threonine-protein kinase/endoribonuclease IRE1
- Molecular Weight
- 109734.08 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 15, 2010 21:21 / Updated at August 26, 2024 19:22