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ID: ALA3797516
Max Phase: Preclinical
Molecular Formula: C15H15NO4
Molecular Weight: 273.29
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1ccc(C(=O)NO)cc1OCc1ccccc1
Standard InChI: InChI=1S/C15H15NO4/c1-19-13-8-7-12(15(17)16-18)9-14(13)20-10-11-5-3-2-4-6-11/h2-9,18H,10H2,1H3,(H,16,17)
Standard InChI Key: IGVRDNCZCPXENL-UHFFFAOYSA-N
Associated Targets(Human)
HDAC8 Tclin Histone deacetylase 8 (4516 Activities)
HDAC1 Tclin Histone deacetylase 1 (10854 Activities)
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HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
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HEK293 (82097 Activities)
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BE(2)-C (181 Activities)
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SMPD1 Tchem Sphingomyelin phosphodiesterase (13561 Activities)
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Associated Targets(non-human)
HDAC8 Histone deacetylase 8 (483 Activities)
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 273.29 | Molecular Weight (Monoisotopic): 273.1001 | AlogP: 2.39 | #Rotatable Bonds: 5 |
| Polar Surface Area: 67.79 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.20 | CX Basic pKa: | CX LogP: 2.23 | CX LogD: 2.22 |
| Aromatic Rings: 2 | Heavy Atoms: 20 | QED Weighted: 0.65 | Np Likeness Score: -0.62 |
References
| 1. Heimburg T, Chakrabarti A, Lancelot J, Marek M, Melesina J, Hauser AT, Shaik TB, Duclaud S, Robaa D, Erdmann F, Schmidt M, Romier C, Pierce RJ, Jung M, Sippl W.. (2016) Structure-Based Design and Synthesis of Novel Inhibitors Targeting HDAC8 from Schistosoma mansoni for the Treatment of Schistosomiasis., 59 (6): [PMID:26937828] [10.1021/acs.jmedchem.5b01478] |
| 2. Ballante F, Reddy DR, Zhou NJ, Marshall GR.. (2017) Structural insights of SmKDAC8 inhibitors: Targeting Schistosoma epigenetics through a combined structure-based 3D QSAR, in vitro and synthesis strategy., 25 (7): [PMID:28259528] [10.1016/j.bmc.2017.02.020] |
| 3. Heimburg T, Kolbinger FR, Zeyen P, Ghazy E, Herp D, Schmidtkunz K, Melesina J, Shaik TB, Erdmann F, Schmidt M, Romier C, Robaa D, Witt O, Oehme I, Jung M, Sippl W.. (2017) Structure-Based Design and Biological Characterization of Selective Histone Deacetylase 8 (HDAC8) Inhibitors with Anti-Neuroblastoma Activity., 60 (24): [PMID:29190092] [10.1021/acs.jmedchem.7b01447] |
| 4. Yang K, Nong K, Gu Q, Dong J, Wang J.. (2018) Discovery of N-hydroxy-3-alkoxybenzamides as direct acid sphingomyelinase inhibitors using a ligand-based pharmacophore model., 151 [PMID:29649738] [10.1016/j.ejmech.2018.03.065] |
Source
Source(1):