1-(5-OXO-2,3,5,9B-TETRAHYDRO-1H-PYRROLO[2,1-A]ISOINDOL-9-YL)-3-(5-PYRROLIDIN-2-YL-1H-PYRAZOL-3-YL)-UREA
Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- 1-(5-OXO-2,3,5,9B-TETRAHYDRO-1H-PYRROLO[2,1-A]ISOINDOL-9-YL)-3-(5-PYRROLIDIN-2-YL-1H-PYRAZOL-3-YL)-UREA
- DrugBank Accession Number
- DB06976
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 1-(5-OXO-2,3,5,9B-TETRAHYDRO-1H-PYRROLO[2,1-A]ISOINDOL-9-YL)-3-(5-PYRROLIDIN-2-YL-1H-PYRAZOL-3-YL)-UREA (DB06976)
- Weight
- Average: 366.417
Monoisotopic: 366.180423978 - Chemical Formula
- C19H22N6O2
- 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 isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Isoindoles and derivatives
- Sub Class
- Isoindolines
- Direct Parent
- Isoindolones
- Alternative Parents
- Aralkylamines / Benzenoids / Imidolactams / Tertiary carboxylic acid amides / Heteroaromatic compounds / Pyrrolidines / Pyrazoles / Ureas / Lactams / Amino acids and derivatives show 6 more
- Substituents
- Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxamide group show 18 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
- IWOOJEZSDPRYAZ-WFASDCNBSA-N
- InChI
- InChI=1S/C19H22N6O2/c26-18-11-4-1-5-13(17(11)15-7-3-9-25(15)18)21-19(27)22-16-10-14(23-24-16)12-6-2-8-20-12/h1,4-5,10,12,15,20H,2-3,6-9H2,(H3,21,22,23,24,27)/t12-,15-/m0/s1
- IUPAC Name
- 3-[(9bS)-5-oxo-1H,2H,3H,5H,9bH-benzo[a]pyrrolizin-9-yl]-1-{5-[(2S)-pyrrolidin-2-yl]-1H-pyrazol-3-yl}urea
- SMILES
- [H][C@]1(CCCN1)C1=CC(NC(=O)NC2=CC=CC3=C2[C@]2([H])CCCN2C3=O)=NN1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 445841
- PubChem Substance
- 99443447
- ChemSpider
- 393357
- BindingDB
- 6631
- ChEMBL
- CHEMBL359020
- ZINC
- ZINC000005974264
- PDBe Ligand
- 2PU
- PDB Entries
- 1gij
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 0.0395 mg/mL ALOGPS logP 1.21 ALOGPS logP 1.27 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 10.43 Chemaxon pKa (Strongest Basic) 9.21 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 102.15 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 105.03 m3·mol-1 Chemaxon Polarizability 39.94 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 + 0.9943 Blood Brain Barrier + 0.9856 Caco-2 permeable - 0.6109 P-glycoprotein substrate Substrate 0.559 P-glycoprotein inhibitor I Non-inhibitor 0.8252 P-glycoprotein inhibitor II Non-inhibitor 0.9643 Renal organic cation transporter Non-inhibitor 0.8272 CYP450 2C9 substrate Non-substrate 0.7863 CYP450 2D6 substrate Non-substrate 0.7843 CYP450 3A4 substrate Non-substrate 0.562 CYP450 1A2 substrate Non-inhibitor 0.5798 CYP450 2C9 inhibitor Non-inhibitor 0.7337 CYP450 2D6 inhibitor Non-inhibitor 0.7881 CYP450 2C19 inhibitor Non-inhibitor 0.5127 CYP450 3A4 inhibitor Non-inhibitor 0.955 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6975 Ames test AMES toxic 0.5079 Carcinogenicity Non-carcinogens 0.8265 Biodegradation Not ready biodegradable 0.9755 Rat acute toxicity 2.4180 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8343 hERG inhibition (predictor II) Inhibitor 0.5201
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-0009000000-ee9001c4a378d5fe2c1f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0923000000-6a17b63860ddf61cb51c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-0509000000-269057ac8c936f544d77 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0019-5921000000-98c0a0da9577127415ef Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0uy1-2926000000-85d2bbd1b77796fe0384 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00kr-2932000000-5ef528089505eab0526c 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]- 179.84517 predictedDeepCCS 1.0 (2019) [M+H]+ 182.20317 predictedDeepCCS 1.0 (2019) [M+Na]+ 189.97023 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 21:18 / Updated at June 12, 2020 16:52