2-Cyclopropyl-5-methyl-N-[4-(trifluoromethyl)phenyl][1,2,4]-triazolo[1,5-a]pyrimidin-7-amine

ID: ALA1956278

Chembl Id: CHEMBL1956278

PubChem CID: 51347692

Max Phase: Preclinical

Molecular Formula: C16H14F3N5

Molecular Weight: 333.32

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1cc(Nc2ccc(C(F)(F)F)cc2)n2nc(C3CC3)nc2n1

Standard InChI:  InChI=1S/C16H14F3N5/c1-9-8-13(21-12-6-4-11(5-7-12)16(17,18)19)24-15(20-9)22-14(23-24)10-2-3-10/h4-8,10,21H,2-3H2,1H3

Standard InChI Key:  TZMPAXWVWBRVRY-UHFFFAOYSA-N

Associated Targets(Human)

Liver microsomes (16955 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasma (7708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHODH Tclin Dihydroorotate dehydrogenase (2737 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Liver (8163 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
dhod Dihydroorotate dehydrogenase (710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dihydroorotate dehydrogenase (quinone), mitochondrial (90 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: 333.32Molecular Weight (Monoisotopic): 333.1201AlogP: 4.07#Rotatable Bonds: 3
Polar Surface Area: 55.11Molecular Species: NEUTRALHBA: 5HBD: 1
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 0.34CX LogP: 3.97CX LogD: 3.97
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.78Np Likeness Score: -2.00

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.  (2016)  Antimalarial agents that are inhibitors of dihydroorotate dehydrogenase,