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Identification
- Generic Name
- 3-({2-[(4-{[6-(CYCLOHEXYLMETHOXY)-9H-PURIN-2-YL]AMINO}PHENYL)SULFONYL]ETHYL}AMINO)PROPAN-1-OL
- DrugBank Accession Number
- DB08309
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 3-({2-[(4-{[6-(CYCLOHEXYLMETHOXY)-9H-PURIN-2-YL]AMINO}PHENYL)SULFONYL]ETHYL}AMINO)PROPAN-1-OL (DB08309)
- Weight
- Average: 488.603
Monoisotopic: 488.220574232 - Chemical Formula
- C23H32N6O4S
- 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 UCyclin-A2 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 hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- Hypoxanthines
- Alternative Parents
- Benzenesulfonyl compounds / Aniline and substituted anilines / Aminopyrimidines and derivatives / Alkyl aryl ethers / Sulfones / Imidazoles / Heteroaromatic compounds / 1,3-aminoalcohols / Dialkylamines / Azacyclic compounds show 4 more
- Substituents
- 1,3-aminoalcohol / Alcohol / Alkanolamine / Alkyl aryl ether / Amine / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Azole show 21 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
- AMFGILNPFBVREA-UHFFFAOYSA-N
- InChI
- InChI=1S/C23H32N6O4S/c30-13-4-11-24-12-14-34(31,32)19-9-7-18(8-10-19)27-23-28-21-20(25-16-26-21)22(29-23)33-15-17-5-2-1-3-6-17/h7-10,16-17,24,30H,1-6,11-15H2,(H2,25,26,27,28,29)
- IUPAC Name
- 3-{[2-(4-{[6-(cyclohexylmethoxy)-9H-purin-2-yl]amino}benzenesulfonyl)ethyl]amino}propan-1-ol
- SMILES
- OCCCNCCS(=O)(=O)C1=CC=C(NC2=NC(OCC3CCCCC3)=C3N=CNC3=N2)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 6852201
- PubChem Substance
- 99444780
- ChemSpider
- 5254654
- ZINC
- ZINC000016052683
- PDBe Ligand
- NU5
- PDB Entries
- 2g9x
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 0.0305 mg/mL ALOGPS logP 2.74 ALOGPS logP 2.04 Chemaxon logS -4.2 ALOGPS pKa (Strongest Acidic) 9.01 Chemaxon pKa (Strongest Basic) 8.04 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 142.12 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 129.93 m3·mol-1 Chemaxon Polarizability 52.98 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9418 Blood Brain Barrier - 0.5829 Caco-2 permeable - 0.6725 P-glycoprotein substrate Substrate 0.6264 P-glycoprotein inhibitor I Non-inhibitor 0.5828 P-glycoprotein inhibitor II Non-inhibitor 0.886 Renal organic cation transporter Non-inhibitor 0.7225 CYP450 2C9 substrate Non-substrate 0.7238 CYP450 2D6 substrate Non-substrate 0.7861 CYP450 3A4 substrate Non-substrate 0.5143 CYP450 1A2 substrate Non-inhibitor 0.8134 CYP450 2C9 inhibitor Non-inhibitor 0.6475 CYP450 2D6 inhibitor Non-inhibitor 0.8701 CYP450 2C19 inhibitor Non-inhibitor 0.7414 CYP450 3A4 inhibitor Non-inhibitor 0.5841 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6481 Ames test Non AMES toxic 0.6063 Carcinogenicity Non-carcinogens 0.6842 Biodegradation Not ready biodegradable 0.9696 Rat acute toxicity 2.4225 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7354 hERG inhibition (predictor II) Inhibitor 0.618
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03dr-0000900000-cc8c0a0f1dd6acac0c0a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0000900000-40e05a39b44243985a6d Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05fu-9000300000-48ba83d1dad1cfcda964 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0019700000-ea2337061848f57a20a4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-052b-9000200000-957a1c8fb38c6d572737 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0019100000-193389398f3da2677c49 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]- 222.55322 predictedDeepCCS 1.0 (2019) [M+H]+ 224.91122 predictedDeepCCS 1.0 (2019) [M+Na]+ 231.58699 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cyclin which controls both the G1/S and the G2/M transition phases of the cell cycle. Functions through the formation of specific serine/threonine protein kinase holoenzyme complexes with the cyclin-dependent protein kinases CDK1 or CDK2. The cyclin subunit confers the substrate specificity of these complexes and differentially interacts with and activates CDK1 and CDK2 throughout the cell cycle
- Specific Function
- Cyclin-dependent protein serine/threonine kinase regulator activity
- Gene Name
- CCNA2
- Uniprot ID
- P20248
- Uniprot Name
- Cyclin-A2
- Molecular Weight
- 48550.365 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 21:30 / Updated at June 12, 2020 16:52