US9238653, Table 5, Compound 41

ID: ALA3689094

Chembl Id: CHEMBL3689094

PubChem CID: 51349278

Max Phase: Preclinical

Molecular Formula: C17H16F3N5

Molecular Weight: 347.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(NC2CCc3ccccc3C2)n2nc(C(F)(F)F)nc2n1

Standard InChI:  InChI=1S/C17H16F3N5/c1-10-8-14(25-16(21-10)23-15(24-25)17(18,19)20)22-13-7-6-11-4-2-3-5-12(11)9-13/h2-5,8,13,22H,6-7,9H2,1H3

Standard InChI Key:  SEOYKFZOPSMBHI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3689094

   5-methyl-N-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 347.34

Molecular Weight (Monoisotopic): 347.1358

AlogP: 3.42

#Rotatable Bonds: 2

Polar Surface Area: 55.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.77

Np Likeness Score: -1.72

References

1.  (2016)  Antimalarial agents that are inhibitors of dihydroorotate dehydrogenase, 

2. Kokkonda S,Deng X,White KL,Coteron JM,Marco M,de Las Heras L,White J,El Mazouni F,Tomchick DR,Manjalanagara K,Rudra KR,Chen G,Morizzi J,Ryan E,Kaminsky W,Leroy D,Martínez-Martínez MS,Jimenez-Diaz MB,Bazaga SF,Angulo-Barturen I,Waterson D,Burrows JN,Matthews D,Charman SA,Phillips MA,Rathod PK.  (2016)  Tetrahydro-2-naphthyl and 2-Indanyl Triazolopyrimidines Targeting Plasmodium falciparum Dihydroorotate Dehydrogenase Display Potent and Selective Antimalarial Activity.,  59  (11.0): [PMID:27127993] [10.1021/acs.jmedchem.6b00275]

Source

Source(2):

• Scientific Literature
• BindingDB Database