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ID: ALA154258
Max Phase: Preclinical
Molecular Formula: C19H21N5O2
Molecular Weight: 351.41
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CCOC(=O)c1ccc(CNc2ccc3nc(N)nc(N)c3c2C)cc1
Standard InChI: InChI=1S/C19H21N5O2/c1-3-26-18(25)13-6-4-12(5-7-13)10-22-14-8-9-15-16(11(14)2)17(20)24-19(21)23-15/h4-9,22H,3,10H2,1-2H3,(H4,20,21,23,24)
Standard InChI Key: PDIOIVDRJWCBMY-UHFFFAOYSA-N
Associated Targets(Human)
Dihydrofolate reductase 3072 Activities
Associated Targets(non-human)
Dihydrofolate reductase 711 Activities
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Thymidylate synthase 842 Activities
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Thymidylate synthase 501 Activities
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Dihydrofolate reductase 93 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: 351.41 | Molecular Weight (Monoisotopic): 351.1695 | AlogP: 2.89 | #Rotatable Bonds: 5 |
| Polar Surface Area: 116.15 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 5 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 7.98 | CX LogP: 3.11 | CX LogD: 2.45 |
| Aromatic Rings: 3 | Heavy Atoms: 26 | QED Weighted: 0.61 | Np Likeness Score: -0.98 |
References
| 1. Crippen GM.. (1980) Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors., 23 (6): [PMID:7392027] [10.1021/jm00180a004] |
| 2. Ghose AK, Crippen GM.. (1982) Quantitative structure-activity relationship by distance geometry: quinazolines as dihydrofolate reductase inhibitors., 25 (8): [PMID:7120278] [10.1021/jm00350a003] |
| 3. Chen BK, Horváth C, Bertino JR.. (1979) Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines., 22 (5): [PMID:110930] [10.1021/jm00191a005] |
| 4. Hansch C, Fukunaga JY, Jow PY.. (1977) Quantitative structure-activity relationships of antimalarial and dihydrofolate reductase inhibition by quinazolines and 5-substituted benzyl-2,4-diaminopyrimidines., 20 (1): [PMID:319234] [10.1021/jm00211a020] |
Source
Source(1):