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ID: ALA5219030
PubChem CID: 168298101
Max Phase: Preclinical
Molecular Formula: C24H25ClN4O2
Molecular Weight: 436.94
Associated Items:
Canonical SMILES: O=C(Nc1ccc2[nH]ccc2n1)[C@H]1CCCN1C(=O)C1(c2cccc(Cl)c2)CCCC1
Standard InChI: InChI=1S/C24H25ClN4O2/c25-17-6-3-5-16(15-17)24(11-1-2-12-24)23(31)29-14-4-7-20(29)22(30)28-21-9-8-18-19(27-21)10-13-26-18/h3,5-6,8-10,13,15,20,26H,1-2,4,7,11-12,14H2,(H,27,28,30)/t20-/m1/s1
Standard InChI Key: SYMFYEMMYNRHSJ-HXUWFJFHSA-N
Molfile:
RDKit 2D 31 35 0 0 0 0 0 0 0 0999 V2000 0.8566 -2.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0850 -1.8712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1243 -1.0471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5195 -0.5309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2886 -0.8303 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9325 -0.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6970 -0.6133 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3433 -0.1011 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2176 0.7178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4485 1.0169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8073 0.5017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3942 0.2848 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9201 -0.8299 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3727 -1.5196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2522 -0.0743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7639 0.5910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0726 0.0158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8214 -0.7699 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4911 -1.2516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1964 -0.7480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8975 0.0197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4815 0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0657 1.4451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4744 2.1593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3000 2.1631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7154 1.4547 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3105 0.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5407 1.4547 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -3.9576 1.0905 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1611 -0.2346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5407 0.5019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 6 5 4 1 0 6 5 1 0 6 7 1 0 7 8 2 0 9 8 1 0 10 9 2 0 10 11 1 0 11 6 2 0 4 12 2 0 13 3 1 0 13 14 1 0 14 1 1 0 13 15 1 0 15 16 2 0 15 17 1 0 17 18 1 0 19 18 1 0 20 19 1 0 21 20 1 0 17 21 1 0 22 17 1 0 23 22 2 0 24 23 1 0 25 24 2 0 26 25 1 0 27 26 2 0 22 27 1 0 26 28 1 0 9 29 1 0 8 30 1 0 30 31 2 0 31 29 1 0 M END
Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
Molecule Type: | Topical: No | First In Class: No | Black Box: No |
Chirality: No | Availability: No | Prodrug: No |
Molecular Weight: 436.94 | Molecular Weight (Monoisotopic): 436.1666 | AlogP: 4.66 | #Rotatable Bonds: 4 |
Polar Surface Area: 78.09 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 2 |
#RO5 Violations: ┄ | HBA (Lipinski): 6 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: 12.18 | CX Basic pKa: 3.63 | CX LogP: 4.77 | CX LogD: 4.77 |
Aromatic Rings: 3 | Heavy Atoms: 31 | QED Weighted: 0.62 | Np Likeness Score: -1.44 |
1. Tian X, Suarez D, Thomson D, Li W, King EA, LaFrance L, Boehm J, Barton L, Di Marco C, Martyr C, Thalji R, Medina J, Knight S, Heerding D, Gao E, Nartey E, Cecconie T, Nixon C, Zhang G, Berrodin TJ, Phelps C, Patel A, Bai X, Lind K, Prabhu N, Messer J, Zhu Z, Shewchuk L, Reid R, Graves AP, McHugh C, Mangatt B.. (2022) Discovery of Proline-Based p300/CBP Inhibitors Using DNA-Encoded Library Technology in Combination with High-Throughput Screening., 65 (21.0): [PMID:36302181] [10.1021/acs.jmedchem.2c00670] |
2. Ravindra, Kodihalli C KC and 9 more authors. 2009-09-04 Inhibition of lysine acetyltransferase KAT3B/p300 activity by a naturally occurring hydroxynaphthoquinone, plumbagin. [PMID:19570987] |
3. Bowers, Erin M and 18 more authors. 2010-05-28 Virtual ligand screening of the p300/CBP histone acetyltransferase: identification of a selective small molecule inhibitor. [PMID:20534345] |
4. Dahlin, Jayme L and 7 more authors. 2015-03-12 PAINS in the assay: chemical mechanisms of assay interference and promiscuous enzymatic inhibition observed during a sulfhydryl-scavenging HTS. [PMID:25634295] |
5. Milite, Ciro C and 10 more authors. 2015-03-26 A novel cell-permeable, selective, and noncompetitive inhibitor of KAT3 histone acetyltransferases from a combined molecular pruning/classical isosterism approach. [PMID:25730130] |
6. Crawford, Terry D TD and 44 more authors. 2016-12-08 Discovery of a Potent and Selective in Vivo Probe (GNE-272) for the Bromodomains of CBP/EP300. [PMID:27682507] |
7. Zhao, Yujun Y and 15 more authors. 2017-05-11 Structure-Based Discovery of 4-(6-Methoxy-2-methyl-4-(quinolin-4-yl)-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole (CD161) as a Potent and Orally Bioavailable BET Bromodomain Inhibitor. [PMID:28463487] |
8. Buuh, Zakey Yusuf ZY, Lyu, Zhigang Z and Wang, Rongsheng E RE. 2018-04-26 Interrogating the Roles of Post-Translational Modifications of Non-Histone Proteins. [PMID:28505447] |
9. Moustakim, Moses; Clark, Peter G K; Hay, Duncan A; Dixon, Darren J and Brennan, Paul E. 2016-12-07 Chemical probes and inhibitors of bromodomains outside the BET family. [PMID:29170712] |
10. Xiang, Qiuping Q and 15 more authors. 2018-03-10 Discovery and optimization of 1-(1H-indol-1-yl)ethanone derivatives as CBP/EP300 bromodomain inhibitors for the treatment of castration-resistant prostate cancer. [PMID:29448139] |
11. Zhao, Yujun Y and 19 more authors. 2018-07-26 Structure-Based Discovery of CF53 as a Potent and Orally Bioavailable Bromodomain and Extra-Terminal (BET) Bromodomain Inhibitor. [PMID:30015487] |
12. Li, Jia J, Xi, Wanlin W, Li, Xiaofang X, Sun, Haiying H and Li, Yuyan Y. 2019-04-01 Advances in inhibition of protein-protein interactions targeting hypoxia-inducible factor-1 for cancer therapy. [PMID:30819620] |
13. Liu, Ruiqi R and 8 more authors. 2019-07-09 Design, synthesis, and biological evaluation of a new class of histone acetyltransferase p300 inhibitors. [PMID:31306905] |
14. Wu, Fangrui and 15 more authors. 2020-05-14 Discovery, Structure-Activity Relationship, and Biological Activity of Histone-Competitive Inhibitors of Histone Acetyltransferases P300/CBP. [PMID:32314924] |
15. Li, Yangfeng and 11 more authors. 2020-07-09 Novel Pyrrolopyridone Bromodomain and Extra-Terminal Motif (BET) Inhibitors Effective in Endocrine-Resistant ER+ Breast Cancer with Acquired Resistance to Fulvestrant and Palbociclib. [PMID:32453591] |
16. He, Zhang-Xu and 5 more authors. 2021-01-01 Current development of CBP/p300 inhibitors in the last decade. [PMID:33045661] |
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