| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ID: ALA281412
Max Phase: Preclinical
Molecular Formula: C13H16N4O
Molecular Weight: 244.30
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCc1nc(N)nc(N)c1-c1ccc(OC)cc1
Standard InChI: InChI=1S/C13H16N4O/c1-3-10-11(12(14)17-13(15)16-10)8-4-6-9(18-2)7-5-8/h4-7H,3H2,1-2H3,(H4,14,15,16,17)
Standard InChI Key: SRYOSRABCMAHOE-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: 244.30 | Molecular Weight (Monoisotopic): 244.1324 | AlogP: 1.88 | #Rotatable Bonds: 3 |
| Polar Surface Area: 87.05 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 7.78 | CX LogP: 1.99 | CX LogD: 1.47 |
| Aromatic Rings: 2 | Heavy Atoms: 18 | QED Weighted: 0.86 | Np Likeness Score: -0.58 |
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. 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] |
| 3. 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):