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ID: ALA21778
Max Phase: Preclinical
Molecular Formula: C13H16N4
Molecular Weight: 228.30
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCc1nc(N)nc(N)c1-c1ccc(C)cc1
Standard InChI: InChI=1S/C13H16N4/c1-3-10-11(12(14)17-13(15)16-10)9-6-4-8(2)5-7-9/h4-7H,3H2,1-2H3,(H4,14,15,16,17)
Standard InChI Key: BGGIEUCLTOKUIN-UHFFFAOYSA-N
Associated Targets(Human)
Beta-hexosaminidase subunit alpha 76 Activities
Beta-N-acetyl-D-hexosaminidase-A/B 71 Activities
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Associated Targets(non-human)
Dihydrofolate reductase 1810 Activities
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Plasmodium falciparum 966862 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: 228.30 | Molecular Weight (Monoisotopic): 228.1375 | AlogP: 2.18 | #Rotatable Bonds: 2 |
| Polar Surface Area: 77.82 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 7.78 | CX LogP: 2.66 | CX LogD: 2.14 |
| Aromatic Rings: 2 | Heavy Atoms: 17 | QED Weighted: 0.83 | Np Likeness Score: -0.76 |
References
| 1. Tarnchompoo B, Sirichaiwat C, Phupong W, Intaraudom C, Sirawaraporn W, Kamchonwongpaisan S, Vanichtanankul J, Thebtaranonth Y, Yuthavong Y.. (2002) Development of 2,4-diaminopyrimidines as antimalarials based on inhibition of the S108N and C59R+S108N mutants of dihydrofolate reductase from pyrimethamine-resistant Plasmodium falciparum., 45 (6): [PMID:11881993] [10.1021/jm010131q] |
| 2. Kamchonwongpaisan S, Quarrell R, Charoensetakul N, Ponsinet R, Vilaivan T, Vanichtanankul J, Tarnchompoo B, Sirawaraporn W, Lowe G, Yuthavong Y.. (2004) Inhibitors of multiple mutants of Plasmodium falciparum dihydrofolate reductase and their antimalarial activities., 47 (3): [PMID:14736247] [10.1021/jm030165t] |
| 3. Parenti MD, Pacchioni S, Ferrari AM, Rastelli G.. (2004) Three-dimensional quantitative structure-activity relationship analysis of a set of Plasmodium falciparum dihydrofolate reductase inhibitors using a pharmacophore generation approach., 47 (17): [PMID:15293997] [10.1021/jm040769c] |
| 4. Tropak MB, Zhang J, Yonekawa S, Rigat BA, Aulakh VS, Smith MR, Hwang HJ, Ciufolini MA, Mahuran DJ.. (2015) Pyrimethamine Derivatives: Insight into Binding Mechanism and Improved Enhancement of Mutant β-N-acetylhexosaminidase Activity., 58 (11): [PMID:25984755] [10.1021/jm5017895] |
Source
Source(1):