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ID: ALA4633246
Max Phase: Preclinical
Molecular Formula: C16H16F3N3O
Molecular Weight: 323.32
Molecule Type: Unknown
Associated Items:
Representations
Canonical SMILES: Cc1c(Cc2ccc(C(F)(F)F)nc2)c[nH]c1C(=O)NC1CC1
Standard InChI: InChI=1S/C16H16F3N3O/c1-9-11(8-21-14(9)15(23)22-12-3-4-12)6-10-2-5-13(20-7-10)16(17,18)19/h2,5,7-8,12,21H,3-4,6H2,1H3,(H,22,23)
Standard InChI Key: AFOVOYRODSYDMK-UHFFFAOYSA-N
Associated Targets(Human)
DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
HepG2 (196354 Activities)
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KCNH2 Tclin HERG (29587 Activities)
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SCN5A Tclin Sodium channel protein type V alpha subunit (3462 Activities)
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CACNA1C Tclin Voltage-gated L-type calcium channel alpha-1C subunit (766 Activities)
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KCNA5 Tclin Voltage-gated potassium channel subunit Kv1.5 (1353 Activities)
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ALB Tchem Serum albumin (2651 Activities)
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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
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CYP3A4 Tclin Cytochrome P450 3A4/3A5 (100 Activities)
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Associated Targets(non-human)
Plasmodium falciparum (966862 Activities)
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Dhodh Dihydroorotate dehydrogenase (104 Activities)
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Dhodh Dihydroorotate dehydrogenase (165 Activities)
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L1210 (27553 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Unknown | 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: 323.32 | Molecular Weight (Monoisotopic): 323.1245 | AlogP: 3.22 | #Rotatable Bonds: 4 |
| Polar Surface Area: 57.78 | Molecular Species: NEUTRAL | HBA: 2 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 1.72 | CX LogP: 3.16 | CX LogD: 3.16 |
| Aromatic Rings: 2 | Heavy Atoms: 23 | QED Weighted: 0.91 | Np Likeness Score: -0.97 |
References
| 1. Kokkonda S, Deng X, White KL, El Mazouni F, White J, Shackleford DM, Katneni K, Chiu FCK, Barker H, McLaren J, Crighton E, Chen G, Angulo-Barturen I, Jimenez-Diaz MB, Ferrer S, Huertas-Valentin L, Martinez-Martinez MS, Lafuente-Monasterio MJ, Chittimalla R, Shahi SP, Wittlin S, Waterson D, Burrows JN, Matthews D, Tomchick D, Rathod PK, Palmer MJ, Charman SA, Phillips MA.. (2020) Lead Optimization of a Pyrrole-Based Dihydroorotate Dehydrogenase Inhibitor Series for the Treatment of Malaria., 63 (9): [PMID:32248693] [10.1021/acs.jmedchem.0c00311] |
| 2. Palmer MJ, Deng X, Watts S, Krilov G, Gerasyuto A, Kokkonda S, El Mazouni F, White J, White KL, Striepen J, Bath J, Schindler KA, Yeo T, Shackleford DM, Mok S, Deni I, Lawong A, Huang A, Chen G, Wang W, Jayaseelan J, Katneni K, Patil R, Saunders J, Shahi SP, Chittimalla R, Angulo-Barturen I, Jiménez-Díaz MB, Wittlin S, Tumwebaze PK, Rosenthal PJ, Cooper RA, Aguiar ACC, Guido RVC, Pereira DB, Mittal N, Winzeler EA, Tomchick DR, Laleu B, Burrows JN, Rathod PK, Fidock DA, Charman SA, Phillips MA.. (2021) Potent Antimalarials with Development Potential Identified by Structure-Guided Computational Optimization of a Pyrrole-Based Dihydroorotate Dehydrogenase Inhibitor Series., 64 (9.0): [PMID:33876936] [10.1021/acs.jmedchem.1c00173] |
Source
Source(1):