3-Hydroxy-1-methyl-5-((4-(trifluoromethyl)phenoxy)methyl)-1H-pyrazole-4-carboxylic acid

ID: ALA4539458

PubChem CID: 155550183

Max Phase: Preclinical

Molecular Formula: C13H11F3N2O4

Molecular Weight: 316.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1nc(O)c(C(=O)O)c1COc1ccc(C(F)(F)F)cc1

Standard InChI:  InChI=1S/C13H11F3N2O4/c1-18-9(10(12(20)21)11(19)17-18)6-22-8-4-2-7(3-5-8)13(14,15)16/h2-5H,6H2,1H3,(H,17,19)(H,20,21)

Standard InChI Key:  OOYQPBRMYNLOMN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   10.8059  -17.2976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4689  -16.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2145  -16.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3973  -16.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1429  -16.8197    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9206  -15.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9176  -14.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8059  -18.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9172  -15.3776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6299  -16.0336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1712  -17.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1696  -18.0442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8765  -18.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8726  -19.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5787  -19.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2882  -19.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2871  -18.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5805  -18.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9956  -19.6827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9951  -20.4999    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7036  -19.2746    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7000  -20.0872    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  2  0
  2  3  2  0
  1  2  1  0
  3  4  1  0
  5  1  1  0
  3  6  1  0
  6  7  2  0
  1  8  1  0
  4  9  1  0
  6 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4539458

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 316.24

Molecular Weight (Monoisotopic): 316.0671

AlogP: 2.42

#Rotatable Bonds: 4

Polar Surface Area: 84.58

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.05

CX Basic pKa: ┄

CX LogP: 3.36

CX LogD: -1.52

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.90

Np Likeness Score: -0.97

References

1. Pippione AC, Sainas S, Goyal P, Fritzson I, Cassiano GC, Giraudo A, Giorgis M, Tavella TA, Bagnati R, Rolando B, Caing-Carlsson R, Costa FTM, Andrade CH, Al-Karadaghi S, Boschi D, Friemann R, Lolli ML..  (2019)  Hydroxyazole scaffold-based Plasmodium falciparum dihydroorotate dehydrogenase inhibitors: Synthesis, biological evaluation and X-ray structural studies.,  163  [PMID:30529545] [10.1016/j.ejmech.2018.11.044]

Source

Source(1):

• Scientific Literature