| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ID: ALA2335416
Max Phase: Preclinical
Molecular Formula: C20H25N5O2
Molecular Weight: 367.45
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(C(C)C#Cc2c(C)nc(N)nc2N)cc(N2CCOCC2)c1
Standard InChI: InChI=1S/C20H25N5O2/c1-13(4-5-18-14(2)23-20(22)24-19(18)21)15-10-16(12-17(11-15)26-3)25-6-8-27-9-7-25/h10-13H,6-9H2,1-3H3,(H4,21,22,23,24)
Standard InChI Key: JQPNVLABZWBWEL-UHFFFAOYSA-N
Associated Targets(Human)
Dihydrofolate reductase 3072 Activities
Associated Targets(non-human)
Dihydrofolate reductase 308 Activities
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Dihydrofolate reductase 367 Activities
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Staphylococcus aureus 210822 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: 367.45 | Molecular Weight (Monoisotopic): 367.2008 | AlogP: 1.95 | #Rotatable Bonds: 3 |
| Polar Surface Area: 99.52 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 7.29 | CX LogP: 2.38 | CX LogD: 2.14 |
| Aromatic Rings: 2 | Heavy Atoms: 27 | QED Weighted: 0.80 | Np Likeness Score: -1.05 |
References
| 1. Paulsen JL, Viswanathan K, Wright DL, Anderson AC.. (2013) Structural analysis of the active sites of dihydrofolate reductase from two species of Candida uncovers ligand-induced conformational changes shared among species., 23 (5): [PMID:23375226] [10.1016/j.bmcl.2013.01.008] |
| 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):