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ID: ALA109619
Max Phase: Preclinical
Molecular Formula: C13H18BrN3S
Molecular Weight: 328.28
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCN(CC)/C(S)=N/N=C(\C)c1cccc(Br)c1
Standard InChI: InChI=1S/C13H18BrN3S/c1-4-17(5-2)13(18)16-15-10(3)11-7-6-8-12(14)9-11/h6-9H,4-5H2,1-3H3,(H,16,18)/b15-10+
Standard InChI Key: WVVSECICMVLAQO-XNTDXEJSSA-N
Associated Targets(non-human)
Cruzipain 33337 Activities
Rhodesain 1463 Activities
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Trypanosoma brucei rhodesiense 7991 Activities
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Trypanosoma brucei 78846 Activities
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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: 328.28 | Molecular Weight (Monoisotopic): 327.0405 | AlogP: 3.80 | #Rotatable Bonds: 4 |
| Polar Surface Area: 27.96 | Molecular Species: NEUTRAL | HBA: 2 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 6.67 | CX Basic pKa: 3.40 | CX LogP: 3.64 | CX LogD: 2.98 |
| Aromatic Rings: 1 | Heavy Atoms: 18 | QED Weighted: 0.39 | Np Likeness Score: -1.20 |
References
| 1. Greenbaum DC, Mackey Z, Hansell E, Doyle P, Gut J, Caffrey CR, Lehrman J, Rosenthal PJ, McKerrow JH, Chibale K.. (2004) Synthesis and structure-activity relationships of parasiticidal thiosemicarbazone cysteine protease inhibitors against Plasmodium falciparum, Trypanosoma brucei, and Trypanosoma cruzi., 47 (12): [PMID:15163200] [10.1021/jm030549j] |
| 2. Ettari R, Tamborini L, Angelo IC, Micale N, Pinto A, De Micheli C, Conti P.. (2013) Inhibition of rhodesain as a novel therapeutic modality for human African trypanosomiasis., 56 (14): [PMID:23611656] [10.1021/jm301424d] |
Source
Source(1):