1-p-tolyl-4-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline

ID: ALA1275633

Cas Number: 343372-45-2

PubChem CID: 3310540

Max Phase: Preclinical

Molecular Formula: C17H11F3N4

Molecular Weight: 328.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2nnc3c(C(F)(F)F)nc4ccccc4n23)cc1

Standard InChI:  InChI=1S/C17H11F3N4/c1-10-6-8-11(9-7-10)15-22-23-16-14(17(18,19)20)21-12-4-2-3-5-13(12)24(15)16/h2-9H,1H3

Standard InChI Key:  PDEQZKMFUXKNAX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -5.1056   -3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1068   -4.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3919   -5.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3937   -3.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6784   -3.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6776   -4.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2520   -3.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679   -3.5363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -4.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9639   -5.1849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7942   -5.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9725   -6.0821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6346   -5.3281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3478   -6.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1532   -6.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7066   -7.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538   -7.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6426   -7.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0927   -7.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401   -3.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231   -3.9349    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451   -2.7017    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9603   -2.9398    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0066   -8.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  9  2  0
  6 10  1  0
 11 14  1  0
  3  6  2  0
 14 15  2  0
  9  7  1  0
 15 16  1  0
  1  2  2  0
 16 17  2  0
  7  8  2  0
 17 18  1  0
  8  5  1  0
 18 19  2  0
 19 14  1  0
  9 10  1  0
  7 20  1  0
  5  4  2  0
 20 21  1  0
  4  1  1  0
 20 22  1  0
 20 23  1  0
  2  3  1  0
 17 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1275633

   1-(4-Methylphenyl)-4-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]quinoxaline

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: 328.30

Molecular Weight (Monoisotopic): 328.0936

AlogP: 4.27

#Rotatable Bonds: 1

Polar Surface Area: 43.08

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.94

CX LogP: 3.79

CX LogD: 3.79

Aromatic Rings: 4

Heavy Atoms: 24

QED Weighted: 0.52

Np Likeness Score: -1.64

References

1. Carosati E, Sforna G, Pippi M, Marverti G, Ligabue A, Guerrieri D, Piras S, Guaitoli G, Luciani R, Costi MP, Cruciani G..  (2010)  Ligand-based virtual screening and ADME-tox guided approach to identify triazolo-quinoxalines as folate cycle inhibitors.,  18  (22): [PMID:20951595] [10.1016/j.bmc.2010.09.065]

2. PubChem BioAssay data set, 

3. Antonova-Koch Y, Meister S, Abraham M, Luth MR, Ottilie S, Lukens AK, Sakata-Kato T, Vanaerschot M, Owen E, Jado JC, Maher SP, Calla J, Plouffe D, Zhong Y, Chen K, Chaumeau V, Conway AJ, McNamara CW, Ibanez M, Gagaring K, Serrano FN, Eribez K, Taggard CM, Cheung AL, Lincoln C, Ambachew B, Rouillier M, Siegel D, Nosten F, Kyle DE, Gamo FJ, Zhou Y, Llinás M, Fidock DA, Wirth DF, Burrows J, Campo B, Winzeler EA..  (2018)  Open-source discovery of chemical leads for next-generation chemoprotective antimalarials.,  362  (6419): [PMID:30523084] [10.1126/science.aat9446]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Winzeler Lab Plasmodium Screening Data