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ID: ALA1738786
Max Phase: Preclinical
Molecular Formula: C15H12F5N5
Molecular Weight: 357.29
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Cc1cc(Nc2ccc(C(F)(F)F)cc2)n2nc(C(C)(F)F)nc2n1
Standard InChI: InChI=1S/C15H12F5N5/c1-8-7-11(22-10-5-3-9(4-6-10)15(18,19)20)25-13(21-8)23-12(24-25)14(2,16)17/h3-7,22H,1-2H3
Standard InChI Key: CUCVTDOXQYMYKL-UHFFFAOYSA-N
Associated Targets(Human)
HepG2 (196354 Activities)
Liver microsomes (16955 Activities)
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Plasma (7708 Activities)
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DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
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Associated Targets(non-human)
Plasmodium falciparum (966862 Activities)
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Liver (8163 Activities)
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dhod Dihydroorotate dehydrogenase (710 Activities)
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Mus musculus (284745 Activities)
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L1210 (27553 Activities)
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Plasma (6361 Activities)
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Rattus norvegicus (775804 Activities)
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Plasma (10718 Activities)
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Dhodh Dihydroorotate dehydrogenase (165 Activities)
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Dhodh Dihydroorotate dehydrogenase (104 Activities)
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Dihydroorotate dehydrogenase (quinone), mitochondrial (90 Activities)
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Dihydroorotate dehydrogenase (quinone), mitochondrial (72 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: 357.29 | Molecular Weight (Monoisotopic): 357.1013 | AlogP: 4.31 | #Rotatable Bonds: 3 |
| Polar Surface Area: 55.11 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 4.18 | CX LogD: 4.18 |
| Aromatic Rings: 3 | Heavy Atoms: 25 | QED Weighted: 0.71 | Np Likeness Score: -1.93 |
References
| 1. Coteron JM, Marco M, Esquivias J, Deng X, White KL, White J, Koltun M, El Mazouni F, Kokkonda S, Katneni K, Bhamidipati R, Shackleford DM, Angulo-Barturen I, Ferrer SB, Jiménez-Díaz MB, Gamo FJ, Goldsmith EJ, Charman WN, Bathurst I, Floyd D, Matthews D, Burrows JN, Rathod PK, Charman SA, Phillips MA.. (2011) Structure-guided lead optimization of triazolopyrimidine-ring substituents identifies potent Plasmodium falciparum dihydroorotate dehydrogenase inhibitors with clinical candidate potential., 54 (15): [PMID:21696174] [10.1021/jm200592f] |
| 2. Deng X, Kokkonda S, El Mazouni F, White J, Burrows JN, Kaminsky W, Charman SA, Matthews D, Rathod PK, Phillips MA.. (2014) Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors., 57 (12): [PMID:24801997] [10.1021/jm500481t] |
| 3. (2016) Antimalarial agents that are inhibitors of dihydroorotate dehydrogenase, |
| 4. Boschi D, Pippione AC, Sainas S, Lolli ML.. (2019) Dihydroorotate dehydrogenase inhibitors in anti-infective drug research., 183 [PMID:31557612] [10.1016/j.ejmech.2019.111681] |
Source
Source(2):