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ID: ALA4846089
Max Phase: Preclinical
Molecular Formula: C32H37FN4O4S
Molecular Weight: 592.74
Molecule Type: Unknown
Associated Items:
Representations
Canonical SMILES: CN1CCN(C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@H](/C=C(\F)S(=O)(=O)c2ccccc2)CCc2ccccc2)CC1
Standard InChI: InChI=1S/C32H37FN4O4S/c1-36-19-21-37(22-20-36)32(39)35-29(23-26-13-7-3-8-14-26)31(38)34-27(18-17-25-11-5-2-6-12-25)24-30(33)42(40,41)28-15-9-4-10-16-28/h2-16,24,27,29H,17-23H2,1H3,(H,34,38)(H,35,39)/b30-24+/t27-,29-/m0/s1
Standard InChI Key: XQQZBPLUMPEIJD-OXGCXKMZSA-N
Associated Targets(Human)
HeLa 62764 Activities
Proteasome Macropain subunit 1025 Activities
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Associated Targets(non-human)
Rhodesain 1463 Activities
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Trypanosoma brucei brucei 13300 Activities
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J774.1 238 Activities
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Molecule Features
| 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 |
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: 592.74 | Molecular Weight (Monoisotopic): 592.2520 | AlogP: 3.96 | #Rotatable Bonds: 11 |
| Polar Surface Area: 98.82 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 2 |
| #RO5 Violations: 1 | HBA (Lipinski): 8 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 13.82 | CX Basic pKa: 7.02 | CX LogP: 4.92 | CX LogD: 4.76 |
| Aromatic Rings: 3 | Heavy Atoms: 42 | QED Weighted: 0.35 | Np Likeness Score: -0.57 |
References
| 1. Jung S, Fuchs N, Johe P, Wagner A, Diehl E, Yuliani T, Zimmer C, Barthels F, Zimmermann RA, Klein P, Waigel W, Meyr J, Opatz T, Tenzer S, Distler U, Räder HJ, Kersten C, Engels B, Hellmich UA, Klein J, Schirmeister T.. (2021) Fluorovinylsulfones and -Sulfonates as Potent Covalent Reversible Inhibitors of the Trypanosomal Cysteine Protease Rhodesain: Structure-Activity Relationship, Inhibition Mechanism, Metabolism, and In Vivo Studies., 64 (16.0): [PMID:34378914] [10.1021/acs.jmedchem.1c01002] |
Source
Source(1):