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ID: ALA88734
Max Phase: Preclinical
Molecular Formula: C9H10BrN3S
Molecular Weight: 272.17
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: C/C(=N\N=C(\N)S)c1cccc(Br)c1
Standard InChI: InChI=1S/C9H10BrN3S/c1-6(12-13-9(11)14)7-3-2-4-8(10)5-7/h2-5H,1H3,(H3,11,13,14)/b12-6+
Standard InChI Key: WJQYKRIBWNZUHM-WUXMJOGZSA-N
Associated Targets(non-human)
Cruzipain 33337 Activities
Trypanosoma cruzi 99888 Activities
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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: 272.17 | Molecular Weight (Monoisotopic): 270.9779 | AlogP: 2.42 | #Rotatable Bonds: 2 |
| Polar Surface Area: 50.74 | Molecular Species: NEUTRAL | HBA: 2 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 6.55 | CX Basic pKa: 3.63 | CX LogP: 2.38 | CX LogD: 1.66 |
| Aromatic Rings: 1 | Heavy Atoms: 14 | QED Weighted: 0.37 | Np Likeness Score: -1.14 |
References
| 1. Du X, Guo C, Hansell E, Doyle PS, Caffrey CR, Holler TP, McKerrow JH, Cohen FE.. (2002) Synthesis and structure-activity relationship study of potent trypanocidal thio semicarbazone inhibitors of the trypanosomal cysteine protease cruzain., 45 (13): [PMID:12061873] [10.1021/jm010459j] |
| 2. 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] |
| 3. 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):