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Identification
- Generic Name
- 5-[(4-AMINOCYCLOHEXYL)AMINO]-7-(PROPAN-2-YLAMINO)PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBONITRILE
- DrugBank Accession Number
- DB08140
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 5-[(4-AMINOCYCLOHEXYL)AMINO]-7-(PROPAN-2-YLAMINO)PYRAZOLO[1,5-A]PYRIMIDINE-3-CARBONITRILE (DB08140)
- Weight
- Average: 313.4007
Monoisotopic: 313.201493771 - Chemical Formula
- C16H23N7
- 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 pyrazolo[1,5-a]pyrimidines. These are aromatic heterocyclic compounds containing a pyrazolo[3,4-d]pyrimidine ring system, which consists of a pyrazole ring fused to and sharing exactly one nitrogen atom with a pyrimidine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Pyrazolopyrimidines
- Sub Class
- Pyrazolo[1,5-a]pyrimidines
- Direct Parent
- Pyrazolo[1,5-a]pyrimidines
- Alternative Parents
- Secondary alkylarylamines / Cyclohexylamines / Aminopyrimidines and derivatives / Imidolactams / Pyrazoles / Heteroaromatic compounds / Nitriles / Azacyclic compounds / Organopnictogen compounds / Monoalkylamines show 1 more
- Substituents
- Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonitrile / Cyclohexylamine / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam show 11 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
- FOESVLPZMGVWBM-JOCQHMNTSA-N
- InChI
- InChI=1S/C16H23N7/c1-10(2)20-15-7-14(21-13-5-3-12(18)4-6-13)22-16-11(8-17)9-19-23(15)16/h7,9-10,12-13,20H,3-6,18H2,1-2H3,(H,21,22)/t12-,13-
- IUPAC Name
- 7-[(propan-2-yl)amino]-5-{[(1r,4r)-4-aminocyclohexyl]amino}pyrazolo[1,5-a]pyrimidine-3-carbonitrile
- SMILES
- [H][C@]1(N)CC[C@@]([H])(CC1)NC1=NC2=C(C=NN2C(NC(C)C)=C1)C#N
References
- General References
- Not Available
- External Links
- PDB Entries
- 2vts
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 0.103 mg/mL ALOGPS logP 1.93 ALOGPS logP 1.22 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 18.59 Chemaxon pKa (Strongest Basic) 10.45 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 104.06 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 102.96 m3·mol-1 Chemaxon Polarizability 35.33 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 + 1.0 Blood Brain Barrier + 0.7495 Caco-2 permeable - 0.5484 P-glycoprotein substrate Substrate 0.5545 P-glycoprotein inhibitor I Non-inhibitor 0.7864 P-glycoprotein inhibitor II Non-inhibitor 0.5785 Renal organic cation transporter Non-inhibitor 0.661 CYP450 2C9 substrate Non-substrate 0.8778 CYP450 2D6 substrate Non-substrate 0.8307 CYP450 3A4 substrate Non-substrate 0.5233 CYP450 1A2 substrate Inhibitor 0.7642 CYP450 2C9 inhibitor Non-inhibitor 0.5401 CYP450 2D6 inhibitor Non-inhibitor 0.782 CYP450 2C19 inhibitor Non-inhibitor 0.6277 CYP450 3A4 inhibitor Non-inhibitor 0.7195 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5312 Ames test Non AMES toxic 0.5107 Carcinogenicity Non-carcinogens 0.8492 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5809 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8842 hERG inhibition (predictor II) Non-inhibitor 0.5943
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03dj-0059000000-9c27315d7f47f4869999 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0009000000-df2c2418f34f07fc439e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0039000000-ca9751279abcc55adb29 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0098000000-31e08492ab42aa0ff496 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0090000000-b4e20ce834d75ea9c63c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-2890000000-10fea6d66086d1843110 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]- 175.44289 predictedDeepCCS 1.0 (2019) [M+H]+ 177.80089 predictedDeepCCS 1.0 (2019) [M+Na]+ 184.18452 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 21:28 / Updated at June 12, 2020 16:52