(13R,15S)-13-METHYL-16-OXA-8,9,12,22,24-PENTAAZAHEXACYCLO[15.6.2.16,9.1,12,15.0,2,7.0,21,25]HEPTACOSA-1(24),2,4,6,17(25),18,20-HEPTAENE-23,26-DIONE
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Identification
- Generic Name
- (13R,15S)-13-METHYL-16-OXA-8,9,12,22,24-PENTAAZAHEXACYCLO[15.6.2.16,9.1,12,15.0,2,7.0,21,25]HEPTACOSA-1(24),2,4,6,17(25),18,20-HEPTAENE-23,26-DIONE
- DrugBank Accession Number
- DB06888
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (13R,15S)-13-METHYL-16-OXA-8,9,12,22,24-PENTAAZAHEXACYCLO[15.6.2.16,9.1,12,15.0,2,7.0,21,25]HEPTACOSA-1(24),2,4,6,17(25),18,20-HEPTAENE-23,26-DIONE (DB06888)
- Weight
- Average: 403.4338
Monoisotopic: 403.164439563 - Chemical Formula
- C22H21N5O3
- 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 quinoxalines. These are compounds containing a quinoxaline moiety, a bicyclic heterocycle made up of a benzene ring fused to a pyrazine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazanaphthalenes
- Sub Class
- Benzodiazines
- Direct Parent
- Quinoxalines
- Alternative Parents
- Indazoles / Alkyl aryl ethers / Pyrazolones / Pyrazines / N-alkylpyrrolidines / Benzenoids / Vinylogous amides / Pyrazoles / Heteroaromatic compounds / Trialkylamines show 6 more
- Substituents
- Alkyl aryl ether / Amine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzopyrazole / Ether / Heteroaromatic compound / Hydrocarbon derivative 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
- KBLPHMRCKHFBJB-OLZOCXBDSA-N
- InChI
- InChI=1S/C22H21N5O3/c1-12-10-13-11-26(12)8-9-27-22(29)15-5-2-4-14(18(15)25-27)19-21(28)23-16-6-3-7-17(30-13)20(16)24-19/h2-7,12-13,25H,8-11H2,1H3,(H,23,28)/t12-,13+/m1/s1
- IUPAC Name
- (13R,15S)-13-methyl-16-oxa-8,9,12,22,24-pentaazahexacyclo[15.6.2.1^{6,9}.1^{12,15}.0^{2,7}.0^{21,25}]heptacosa-1(24),2(7),3,5,17,19,21(25)-heptaene-23,27-dione
- SMILES
- [H][C@]12CN(CCN3NC4=C(C=CC=C4C3=O)C3=NC4=C(NC3=O)C=CC=C4O1)[C@]([H])(C)C2
References
- General References
- Not Available
- External Links
- PDB Entries
- 2ds1
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 0.335 mg/mL ALOGPS logP 1.86 ALOGPS logP 2.14 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 8.57 Chemaxon pKa (Strongest Basic) 7.9 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 86.27 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 116.32 m3·mol-1 Chemaxon Polarizability 42.01 Å3 Chemaxon Number of Rings 6 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 + 0.7265 Caco-2 permeable - 0.6081 P-glycoprotein substrate Substrate 0.8071 P-glycoprotein inhibitor I Non-inhibitor 0.5129 P-glycoprotein inhibitor II Non-inhibitor 0.9302 Renal organic cation transporter Non-inhibitor 0.6758 CYP450 2C9 substrate Non-substrate 0.8791 CYP450 2D6 substrate Non-substrate 0.6851 CYP450 3A4 substrate Substrate 0.6624 CYP450 1A2 substrate Non-inhibitor 0.8396 CYP450 2C9 inhibitor Non-inhibitor 0.8381 CYP450 2D6 inhibitor Non-inhibitor 0.7095 CYP450 2C19 inhibitor Non-inhibitor 0.6885 CYP450 3A4 inhibitor Non-inhibitor 0.9182 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7216 Ames test AMES toxic 0.5277 Carcinogenicity Non-carcinogens 0.7898 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6409 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7555 hERG inhibition (predictor II) Non-inhibitor 0.6733
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-01ri-0009100000-467ef8d0aca9c00ced91 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0000900000-b4ca4e42009366a88eba Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0000900000-f0904e7210bdeba7f74e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0002900000-61b322d1fa6f35fa4deb Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0000900000-443cb5e1f44a1f07a5e2 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01u9-0009000000-38d70fdf40f66b4838c1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-006x-6009000000-bae20727945ca75abc02 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]- 190.32155 predictedDeepCCS 1.0 (2019) [M+H]+ 192.67955 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.1154 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 21:17 / Updated at June 12, 2020 16:52