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ID: ALA56101
Max Phase: Preclinical
Molecular Formula: C17H16N4
Molecular Weight: 276.34
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Nc1ncc(Cc2ccc(-c3ccccc3)cc2)c(N)n1
Standard InChI: InChI=1S/C17H16N4/c18-16-15(11-20-17(19)21-16)10-12-6-8-14(9-7-12)13-4-2-1-3-5-13/h1-9,11H,10H2,(H4,18,19,20,21)
Standard InChI Key: UVFCOEHLSTZCHI-UHFFFAOYSA-N
Associated Targets(non-human)
Dihydrofolate reductase 1415 Activities
Dihydrofolate reductase 59 Activities
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Dihydrofolate reductase 640 Activities
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Dihydrofolate reductase 392 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 |
|---|
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: 276.34 | Molecular Weight (Monoisotopic): 276.1375 | AlogP: 2.90 | #Rotatable Bonds: 3 |
| 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: 7.16 | CX LogP: 3.40 | CX LogD: 3.22 |
| Aromatic Rings: 3 | Heavy Atoms: 21 | QED Weighted: 0.77 | Np Likeness Score: -0.32 |
References
| 1. Selassie CD, Fang ZX, Li RL, Hansch C, Debnath G, Klein TE, Langridge R, Kaufman BT.. (1989) On the structure selectivity problem in drug design. A comparative study of benzylpyrimidine inhibition of vertebrate and bacterial dihydrofolate reductase via molecular graphics and quantitative structure-activity relationships., 32 (8): [PMID:2502631] [10.1021/jm00128a035] |
| 2. Loukas YL.. (2001) Adaptive neuro-fuzzy inference system: an instant and architecture-free predictor for improved QSAR studies., 44 (17): [PMID:11495588] [10.1021/jm000226c] |
| 3. So SS, Richards WG.. (1992) Application of neural networks: quantitative structure-activity relationships of the derivatives of 2,4-diamino-5-(substituted-benzyl)pyrimidines as DHFR inhibitors., 35 (17): [PMID:1507206] [10.1021/jm00095a016] |
| 4. Dunn WJ, Hopfinger AJ, Catana C, Duraiswami C.. (1996) Solution of the conformation and alignment tensors for the binding of trimethoprim and its analogs to dihydrofolate reductase: 3D-quantitative structure-activity relationship study using molecular shape analysis, 3-way partial least-squares regression, and 3-way factor analysis., 39 (24): [PMID:8941396] [10.1021/jm960491r] |
| 5. Selassie CD, Li RL, Poe M, Hansch C.. (1991) On the optimization of hydrophobic and hydrophilic substituent interactions of 2,4-diamino-5-(substituted-benzyl)pyrimidines with dihydrofolate reductase., 34 (1): [PMID:1899453] [10.1021/jm00105a008] |
Source
Source(1):