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ID: ALA575217
Max Phase: Preclinical
Molecular Formula: C24H26N4O
Molecular Weight: 386.50
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(-c2cc(C)cc(C)c2)cc(C(C)C#Cc2c(C)nc(N)nc2N)c1
Standard InChI: InChI=1S/C24H26N4O/c1-14-8-15(2)10-19(9-14)20-11-18(12-21(13-20)29-5)16(3)6-7-22-17(4)27-24(26)28-23(22)25/h8-13,16H,1-5H3,(H4,25,26,27,28)
Standard InChI Key: ATFDKOLABYIYCC-UHFFFAOYSA-N
Associated Targets(Human)
Dihydrofolate reductase 3072 Activities
Associated Targets(non-human)
Dihydrofolate reductase 308 Activities
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Candida albicans 78123 Activities
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Dihydrofolate reductase 367 Activities
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Dihydrofolate reductase 15 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: 386.50 | Molecular Weight (Monoisotopic): 386.2107 | AlogP: 4.40 | #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: 7.29 | CX LogP: 5.17 | CX LogD: 4.92 |
| Aromatic Rings: 3 | Heavy Atoms: 29 | QED Weighted: 0.65 | Np Likeness Score: -0.50 |
References
| 1. Paulsen JL, Liu J, Bolstad DB, Smith AE, Priestley ND, Wright DL, Anderson AC.. (2009) In vitro biological activity and structural analysis of 2,4-diamino-5-(2'-arylpropargyl)pyrimidine inhibitors of Candida albicans., 17 (14): [PMID:19560363] [10.1016/j.bmc.2009.06.021] |
| 2. Zhou W, Viswanathan K, Hill D, Anderson AC, Wright DL.. (2012) Acetylenic linkers in lead compounds: a study of the stability of the propargyl-linked antifolates., 40 (10): [PMID:22815313] [10.1124/dmd.112.046870] |
| 3. (2014) Heterocyclic analogs of propargyl-linked inhibitors of dihydrofolate reductase, |
Source
Source(2):