ID: ALA492529

Max Phase: Preclinical

Molecular Formula: C13H10F3N5

Molecular Weight: 293.25

Molecule Type: Small molecule

Representations

Synonyms (1): DSM-74
Synonyms from Alternative Forms(1):

Canonical SMILES:  Cc1cc(Nc2ccc(C(F)(F)F)cc2)n2ncnc2n1

Standard InChI:  InChI=1S/C13H10F3N5/c1-8-6-11(21-12(19-8)17-7-18-21)20-10-4-2-9(3-5-10)13(14,15)16/h2-7,20H,1H3

Standard InChI Key:  LRHHXKBKRNNFRV-UHFFFAOYSA-N

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

Properties

Molecular Weight: 293.25

Molecular Weight (Monoisotopic): 293.0888

AlogP: 3.20

#Rotatable Bonds: 2

Polar Surface Area: 55.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.75

CX LogD: 2.75

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.79

Np Likeness Score: -2.42

References

1. Gujjar R, Marwaha A, El Mazouni F, White J, White KL, Creason S, Shackleford DM, Baldwin J, Charman WN, Buckner FS, Charman S, Rathod PK, Phillips MA..  (2009)  Identification of a metabolically stable triazolopyrimidine-based dihydroorotate dehydrogenase inhibitor with antimalarial activity in mice.,  52  (7): [PMID:19296651] [10.1021/jm801343r]

2. Gujjar R, El Mazouni F, White KL, White J, Creason S, Shackleford DM, Deng X, Charman WN, Bathurst I, Burrows J, Floyd DM, Matthews D, Buckner FS, Charman SA, Phillips MA, Rathod PK..  (2011)  Lead optimization of aryl and aralkyl amine-based triazolopyrimidine inhibitors of Plasmodium falciparum dihydroorotate dehydrogenase with antimalarial activity in mice.,  54  (11): [PMID:21517059] [10.1021/jm200265b]

3. Deng X, Kokkonda S, El Mazouni F, White J, Burrows JN, Kaminsky W, Charman SA, Matthews D, Rathod PK, Phillips MA..  (2014)  Fluorine modulates species selectivity in the triazolopyrimidine class of Plasmodium falciparum dihydroorotate dehydrogenase inhibitors.,  57  (12): [PMID:24801997] [10.1021/jm500481t]

4. Singh A, Maqbool M, Mobashir M, Hoda N..  (2017)  Dihydroorotate dehydrogenase: A drug target for the development of antimalarials.,  125  [PMID:27721149] [10.1016/j.ejmech.2016.09.085]

5. Boschi D, Pippione AC, Sainas S, Lolli ML..  (2019)  Dihydroorotate dehydrogenase inhibitors in anti-infective drug research.,  183  [PMID:31557612] [10.1016/j.ejmech.2019.111681]

Source

Source(1):

• Scientific Literature