N-cyclopropyl-5-(2-(trifluoromethyl)-1H-benzo[d]imidazol-1-yl)thiophene-2-carboxamide

ID: ALA2012941

PubChem CID: 70685307

Max Phase: Preclinical

Molecular Formula: C16H12F3N3OS

Molecular Weight: 351.35

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  O=C(NC1CC1)c1ccc(-n2c(C(F)(F)F)nc3ccccc32)s1

Standard InChI:  InChI=1S/C16H12F3N3OS/c17-16(18,19)15-21-10-3-1-2-4-11(10)22(15)13-8-7-12(24-13)14(23)20-9-5-6-9/h1-4,7-9H,5-6H2,(H,20,23)

Standard InChI Key:  QURCGBATQHAFAH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   11.8588  -24.0431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6481  -23.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3083  -24.3013    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.9847  -23.8287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7443  -23.0395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9194  -23.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1968  -23.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5204  -24.0157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5857  -24.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7612  -24.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3368  -25.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7356  -26.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5634  -26.2425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9841  -25.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7646  -24.0982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9212  -24.9083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3878  -23.5575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7009  -25.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2120  -22.7181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9340  -22.3189    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.5052  -22.2925    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.2052  -21.8894    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.2394  -25.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5088  -25.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 11 12  2  0
  6  2  2  0
 12 13  1  0
  1  7  1  0
 13 14  2  0
 14  9  1  0
  1  2  1  0
  4 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  2  0
 15 17  2  0
  8 10  1  0
 16 18  1  0
  9  1  1  0
  7 19  1  0
 19 20  1  0
  3  4  1  0
 19 21  1  0
  9 10  2  0
 19 22  1  0
 23 18  1  0
 24 23  1  0
 18 24  1  0
  4  5  2  0
 10 11  1  0
M  END

Associated Targets(Human)

DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPTEC (172 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

dhod Dihydroorotate dehydrogenase (710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: 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: 351.35Molecular Weight (Monoisotopic): 351.0653AlogP: 4.00#Rotatable Bonds: 3
Polar Surface Area: 46.92Molecular Species: NEUTRALHBA: 4HBD: 1
#RO5 Violations: HBA (Lipinski): 4HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 1.88CX LogP: 4.02CX LogD: 4.02
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.78Np Likeness Score: -1.75

References

1. Skerlj RT, Bastos CM, Booker ML, Kramer ML, Barker RH, Celatka CA, O'Shea TJ, Munoz B, Sidhu AB, Cortese JF, Wittlin S, Papastogiannidis P, Angulo-Barturen I, Jimenez-Diaz MB, Sybertz E..  (2011)  Optimization of Potent Inhibitors of P. falciparum Dihydroorotate Dehydrogenase for the Treatment of Malaria.,  (9): [PMID:24900364] [10.1021/ml200143c]

Source