Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- 1-Amino-6-Cyclohex-3-Enylmethyloxypurine
- DrugBank Accession Number
- DB02603
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 1-Amino-6-Cyclohex-3-Enylmethyloxypurine (DB02603)
- Weight
- Average: 246.3082
Monoisotopic: 246.148061218 - Chemical Formula
- C13H18N4O
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism ACyclin-dependent kinase 2 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 imidazo-[4,5-c]pyridines. These are organic heterocyclic compounds containing an imidazo-[4,5-c]pyridine ring system. Imidazo-[4,5-c]pyridine consists of an imidazole ring fused to a pyridine, so that the three ring nitrogen atoms are at the 1-, 2-, and 5-position, respectively.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyridines
- Sub Class
- Imidazo-[4,5-c]pyridines
- Direct Parent
- Imidazo-[4,5-c]pyridines
- Alternative Parents
- Aminopyridines and derivatives / Alkyl aryl ethers / Imidolactams / Imidazoles / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amine / Aminopyridine / Aromatic heteropolycyclic compound / Azacycle / Azole / Ether / Heteroaromatic compound / Hydrocarbon derivative / Imidazo-[4,5-c]pyridine
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- VPUIDVRYMVIXGO-UHFFFAOYSA-N
- InChI
- InChI=1S/C13H18N4O/c14-11-6-10-12(16-8-15-10)13(17-11)18-7-9-4-2-1-3-5-9/h6,8-9H,1-5,7H2,(H2,14,17)(H,15,16)
- IUPAC Name
- 4-(cyclohexylmethoxy)-1H-imidazo[4,5-c]pyridin-6-amine
- SMILES
- NC1=NC(OCC2CCCCC2)=C2N=CNC2=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 445967
- PubChem Substance
- 46508985
- ChemSpider
- 393445
- ZINC
- ZINC000020149007
- PDBe Ligand
- 207
- PDB Entries
- 1h0w
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 0.288 mg/mL ALOGPS logP 2.55 ALOGPS logP 2.36 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 9.23 Chemaxon pKa (Strongest Basic) 5.45 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 76.82 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 70.35 m3·mol-1 Chemaxon Polarizability 27.3 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 + 0.9761 Blood Brain Barrier + 0.9699 Caco-2 permeable - 0.6911 P-glycoprotein substrate Non-substrate 0.6106 P-glycoprotein inhibitor I Non-inhibitor 0.7922 P-glycoprotein inhibitor II Non-inhibitor 0.5804 Renal organic cation transporter Non-inhibitor 0.6821 CYP450 2C9 substrate Non-substrate 0.8477 CYP450 2D6 substrate Non-substrate 0.7739 CYP450 3A4 substrate Non-substrate 0.5941 CYP450 1A2 substrate Inhibitor 0.8063 CYP450 2C9 inhibitor Non-inhibitor 0.5997 CYP450 2D6 inhibitor Inhibitor 0.5642 CYP450 2C19 inhibitor Inhibitor 0.7986 CYP450 3A4 inhibitor Inhibitor 0.7738 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7581 Ames test AMES toxic 0.5729 Carcinogenicity Non-carcinogens 0.9517 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3048 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8702 hERG inhibition (predictor II) Non-inhibitor 0.5356
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-9440000000-95ba37d88b58dc8b97ca Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-9080000000-a95a7d81a711d1a8e544 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0090000000-4f7bbedf0d057734506c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0190000000-6361314046b9db70515c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4j-9210000000-5c8a13be03c082ce9da2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000t-0930000000-d18da78477160919c31c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-052f-7910000000-1acb5e43dd1cf6b1ea42 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]- 167.4340523 predictedDarkChem Lite v0.1.0 [M-H]- 155.80104 predictedDeepCCS 1.0 (2019) [M+H]+ 166.2483523 predictedDarkChem Lite v0.1.0 [M+H]+ 158.15904 predictedDeepCCS 1.0 (2019) [M+Na]+ 167.4045523 predictedDarkChem Lite v0.1.0 [M+Na]+ 164.25218 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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 June 13, 2005 13:24 / Updated at August 26, 2024 19:22