ID: ALA4550833
PubChem CID: 118297736
Max Phase: Preclinical
Molecular Formula: C18H20ClN5O2
Molecular Weight: 373.84
Molecule Type: Unknown
Associated Items:
Canonical SMILES: CCOc1cc(C)ccc1Oc1cccc(Cl)c1CNc1nc(N)n[nH]1
Standard InChI: InChI=1S/C18H20ClN5O2/c1-3-25-16-9-11(2)7-8-15(16)26-14-6-4-5-13(19)12(14)10-21-18-22-17(20)23-24-18/h4-9H,3,10H2,1-2H3,(H4,20,21,22,23,24)
Standard InChI Key: OPWFCBVVTDENIM-UHFFFAOYSA-N
Molfile:
RDKit 2D
26 28 0 0 0 0 0 0 0 0999 V2000
10.6757 -20.5205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
10.6746 -21.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.3826 -21.7490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.0923 -21.3396 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.0895 -20.5169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11.3808 -20.1117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.7956 -20.1057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
13.5049 -20.5116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.5046 -21.3265 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.2130 -21.7323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.9202 -21.3210 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.9144 -20.4996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.2055 -20.0974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.1981 -19.2803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.9022 -18.8654 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
14.8948 -18.0482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.5456 -17.5610 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
15.2862 -16.7861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.4689 -16.7934 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
14.2235 -17.5728 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
15.7606 -16.1207 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
15.6191 -20.0859 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0
11.3784 -19.2945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
12.0849 -18.8838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.0824 -18.0666 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
9.9665 -21.7481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 4 2 0
4 5 1 0
5 6 2 0
6 1 1 0
5 7 1 0
7 8 1 0
8 9 2 0
9 10 1 0
10 11 2 0
11 12 1 0
12 13 2 0
13 8 1 0
13 14 1 0
14 15 1 0
15 16 1 0
16 17 2 0
17 18 1 0
18 19 2 0
19 20 1 0
20 16 1 0
18 21 1 0
12 22 1 0
6 23 1 0
23 24 1 0
24 25 1 0
2 26 1 0
M END| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
|---|
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Unknown | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
|---|
| Molecular Weight: 373.84 | Molecular Weight (Monoisotopic): 373.1306 | AlogP: 4.15 | #Rotatable Bonds: 7 |
| Polar Surface Area: 98.08 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 3 |
| #RO5 Violations: ┄ | HBA (Lipinski): 7 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 13.51 | CX Basic pKa: 3.79 | CX LogP: 4.14 | CX LogD: 4.14 |
| Aromatic Rings: 3 | Heavy Atoms: 26 | QED Weighted: 0.58 | Np Likeness Score: -1.33 |
| 1. Holshouser S, Dunworth M, Murray-Stewart T, Peterson YK, Burger P, Kirkpatrick J, Chen HH, Casero RA, Woster PM.. (2019) Dual inhibitors of LSD1 and spermine oxidase., 10 (5): [PMID:31191868] [10.1039/C8MD00610E] |
| 2. Liang, Yu Y and 5 more authors. 2013-02-05 A novel selective LSD1/KDM1A inhibitor epigenetically blocks herpes simplex virus lytic replication and reactivation from latency. [PMID:23386436] |
| 3. Zheng, Yi-Chao YC and 15 more authors. 2013-11-14 Triazole-dithiocarbamate based selective lysine specific demethylase 1 (LSD1) inactivators inhibit gastric cancer cell growth, invasion, and migration. [PMID:24131029] |
| 4. Sorna, Venkataswamy V and 6 more authors. 2013-12-12 High-throughput virtual screening identifies novel N'-(1-phenylethylidene)-benzohydrazides as potent, specific, and reversible LSD1 inhibitors. [PMID:24237195] |
| 5. Rotili, Dante D and 18 more authors. 2014-01-09 Pan-histone demethylase inhibitors simultaneously targeting Jumonji C and lysine-specific demethylases display high anticancer activities. [PMID:24325601] |
| 6. Kumarasinghe, Isuru R IR and Woster, Patrick M PM. 2014-01-09 Synthesis and evaluation of novel cyclic Peptide inhibitors of lysine-specific demethylase 1. [PMID:24883177] |
| 7. Ma, Li-Ying LY and 17 more authors. 2015-02-26 Design, synthesis, and structure-activity relationship of novel LSD1 inhibitors based on pyrimidine-thiourea hybrids as potent, orally active antitumor agents. [PMID:25610955] |
| 8. Maes, Tamara T and 6 more authors. 2015 KDM1 histone lysine demethylases as targets for treatments of oncological and neurodegenerative disease. [PMID:26111032] |
| 9. Wu, Fangrui F and 6 more authors. 2016-01-14 3-(Piperidin-4-ylmethoxy)pyridine Containing Compounds Are Potent Inhibitors of Lysine Specific Demethylase 1. [PMID:26652247] |
| 10. Amano, Yuichi Y and 6 more authors. 2017-05-01 Development and crystallographic evaluation of histone H3 peptide with N-terminal serine substitution as a potent inhibitor of lysine-specific demethylase 1. [PMID:28336409] |
| 11. Li, Zhong-Hua ZH and 10 more authors. 2017-04-13 Discovery of [1,2,3]Triazolo[4,5-d]pyrimidine Derivatives as Novel LSD1 Inhibitors. [PMID:28435523] |
| 12. Mould, Daniel P DP and 11 more authors. 2017-10-12 Development of (4-Cyanophenyl)glycine Derivatives as Reversible Inhibitors of Lysine Specific Demethylase 1. [PMID:28892629] |
| 13. Mould, Daniel P and 7 more authors. 2017-10-15 Development and evaluation of 4-(pyrrolidin-3-yl)benzonitrile derivatives as inhibitors of lysine specific demethylase 1. [PMID:28927796] |
| 14. Sun, Kai K and 6 more authors. 2017-11-15 Discovery of tranylcypromine analogs with an acylhydrazone substituent as LSD1 inactivators: Design, synthesis and their biological evaluation. [PMID:29037950] |
| 15. and Abdel-Magid, Ahmed F AF. 2017-11-09 Lysine-Specific Demethylase 1 (LSD1) Inhibitors as Potential Treatment for Different Types of Cancers. [PMID:29152043] |
| 16. Schulz-Fincke, Johannes J and 15 more authors. 2018-01-20 Structure-activity studies on N-Substituted tranylcypromine derivatives lead to selective inhibitors of lysine specific demethylase 1 (LSD1) and potent inducers of leukemic cell differentiation. [PMID:29247860] |
| 17. Xu, Siyuan S and 6 more authors. 2018-09-15 Optimization of 5-arylidene barbiturates as potent, selective, reversible LSD1 inhibitors for the treatment of acute promyelocytic leukemia. [PMID:30153955] |
| 18. Nie, Zhe Z and 11 more authors. 2019-01-01 Structure-based design and discovery of potent and selective lysine-specific demethylase 1 (LSD1) inhibitors. [PMID:30409536] |
| 19. Duan, Yingchao Y and 7 more authors. 2018-12-15 Design, synthesis and in vitro evaluation of stilbene derivatives as novel LSD1 inhibitors for AML therapy. [PMID:30448189] |
| 20. Ma, Qi-Sheng QS and 6 more authors. 2019-01-15 Ligand-based design, synthesis and biological evaluation of xanthine derivatives as LSD1/KDM1A inhibitors. [PMID:30472603] |
| 21. Liu, Hong-Min HM and 10 more authors. 2019-08-01 Discovery and synthesis of novel indole derivatives-containing 3-methylenedihydrofuran-2(3H)-one as irreversible LSD1 inhibitors. [PMID:31096156] |
| 22. Holshouser, Steven S and 8 more authors. 2019-05-01 Dual inhibitors of LSD1 and spermine oxidase. [PMID:31191868] |
| 23. Romussi, Alessia and 19 more authors. 2020-05-14 Discovery of Reversible Inhibitors of KDM1A Efficacious in Acute Myeloid Leukemia Models. [PMID:32435381] |
| 24. Dai, Xing-Jie and 5 more authors. 2020-12-10 Tranylcypromine Based Lysine-Specific Demethylase 1 Inhibitor: Summary and Perspective. [PMID:32931269] |
| 25. Kanouni, Toufike and 18 more authors. 2020-12-10 Discovery of CC-90011: A Potent and Selective Reversible Inhibitor of Lysine Specific Demethylase 1 (LSD1). [PMID:33034194] |
| 26. Naveen Sadhu, M and 10 more authors. 2021-02-15 Novel dual LSD1/HDAC6 inhibitors for the treatment of multiple myeloma. [PMID:33359604] |
| 27. Mehndiratta, Samir and Liou, Jing-Ping. 2020-09-01 Histone lysine specific demethylase 1 inhibitors. [PMID:33479691] |
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