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:

This compound is not in our inventory system

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

Alternative Forms

  1. Parent:

    ALA4635646

    ---

Associated Targets(Human)

DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALB Tchem Serum albumin (2651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhodh Dihydroorotate dehydrogenase (104 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhodh Dihydroorotate dehydrogenase (165 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 340.32Molecular Weight (Monoisotopic): 340.1199AlogP: 3.96#Rotatable Bonds: 4
Polar Surface Area: 44.89Molecular Species: NEUTRALHBA: 1HBD: 2
#RO5 Violations: HBA (Lipinski): 3HBD (Lipinski): 2#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 4.14CX LogD: 4.14
Aromatic Rings: 2Heavy Atoms: 24QED Weighted: 0.81Np 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]

Source