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N-Cyclopropyl-4-(2-fluoro-4-(trifluoromethyl)benzyl)-3-methyl-1H-pyrrole-2-carboxamide
ID: ALA4635646
PubChem CID: 146020610
Max Phase: Preclinical
Molecular Formula: C17H16F4N2O
Molecular Weight: 340.32
Molecule Type: Unknown
Associated Items:
Names and Identifiers
Canonical SMILES: Cc1c(Cc2ccc(C(F)(F)F)cc2F)c[nH]c1C(=O)NC1CC1
Standard InChI: InChI=1S/C17H16F4N2O/c1-9-11(8-22-15(9)16(24)23-13-4-5-13)6-10-2-3-12(7-14(10)18)17(19,20)21/h2-3,7-8,13,22H,4-6H2,1H3,(H,23,24)
Standard InChI Key: HLDSAPKKTAWHGH-UHFFFAOYSA-N
Molfile:
RDKit 2D
24 26 0 0 0 0 0 0 0 0999 V2000
31.9394 -27.3348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
31.7330 -28.0984 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
32.3917 -28.5296 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
33.0040 -28.0304 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
32.7265 -27.2996 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
33.7636 -28.2450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
33.9678 -29.0063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
31.3613 -26.7269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
30.5434 -26.9187 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.9730 -26.3030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.1558 -26.4942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
28.9112 -27.2989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.4944 -27.9124 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
30.3093 -27.7178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
28.0926 -27.4921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
27.5172 -26.8800 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
27.8536 -28.2972 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
27.2769 -27.7061 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
34.3452 -27.6751 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
35.1324 -27.8947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
35.7055 -28.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
35.9250 -27.6879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
33.1755 -26.6167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
30.2120 -25.5215 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 4 1 0
4 5 2 0
5 1 1 0
4 6 1 0
6 7 2 0
1 8 1 0
8 9 1 0
9 10 2 0
10 11 1 0
11 12 2 0
12 13 1 0
13 14 2 0
14 9 1 0
12 15 1 0
15 16 1 0
15 17 1 0
15 18 1 0
6 19 1 0
19 20 1 0
21 20 1 0
22 21 1 0
20 22 1 0
5 23 1 0
10 24 1 0
M END
Associated Targets(Human)
Associated Targets(non-human)
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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Calculated Properties
Molecular Weight: 340.32 | Molecular Weight (Monoisotopic): 340.1199 | AlogP: 3.96 | #Rotatable Bonds: 4 |
Polar Surface Area: 44.89 | Molecular Species: NEUTRAL | HBA: 1 | HBD: 2 |
#RO5 Violations: ┄ | HBA (Lipinski): 3 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: ┄ | CX Basic pKa: ┄ | CX LogP: 4.14 | CX LogD: 4.14 |
Aromatic Rings: 2 | Heavy Atoms: 24 | QED Weighted: 0.81 | Np Likeness Score: -1.12 |
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] |