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ID: ALA172782
Max Phase: Preclinical
Molecular Formula: C18H14N2O2
Molecular Weight: 290.32
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COC(=O)/C(C#N)=C/c1ccc(/C=C/c2ccccn2)cc1
Standard InChI: InChI=1S/C18H14N2O2/c1-22-18(21)16(13-19)12-15-7-5-14(6-8-15)9-10-17-4-2-3-11-20-17/h2-12H,1H3/b10-9+,16-12+
Standard InChI Key: RTSXZTUPJDTHHB-HMSDUJDUSA-N
Associated Targets(Human)
Dihydrofolate reductase 3072 Activities
Associated Targets(non-human)
Leishmania donovani 89745 Activities
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Trypanosoma brucei 78846 Activities
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Trypanosoma cruzi 99888 Activities
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Dihydrofolate reductase 126 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: 290.32 | Molecular Weight (Monoisotopic): 290.1055 | AlogP: 3.33 | #Rotatable Bonds: 4 |
| Polar Surface Area: 62.98 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 4.67 | CX LogP: 3.68 | CX LogD: 3.68 |
| Aromatic Rings: 2 | Heavy Atoms: 22 | QED Weighted: 0.49 | Np Likeness Score: -0.84 |
References
| 1. Chowdhury SF, Di Lucrezia R, Guerrero RH, Brun R, Goodman J, Ruiz-Perez LM, Pacanowska DG, Gilbert IH.. (2001) Novel inhibitors of Leishmanial dihydrofolate reductase., 11 (8): [PMID:11327604] [10.1016/s0960-894x(01)00089-0] |
| 2. Bibi M,Qureshi NA,Sadiq A,Farooq U,Hassan A,Shaheen N,Asghar I,Umer D,Ullah A,Khan FA,Salman M,Bibi A,Rashid U. (2021) Exploring the ability of dihydropyrimidine-5-carboxamide and 5-benzyl-2,4-diaminopyrimidine-based analogues for the selective inhibition of L. major dihydrofolate reductase., 210 [PMID:33187806] [10.1016/j.ejmech.2020.112986] |
Source
Source(1):