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

ID: ALA4458056

PubChem CID: 85469100

Max Phase: Preclinical

Molecular Formula: C13H11F3N2O4

Molecular Weight: 316.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1nc(O)c(C(=O)O)c1COc1cccc(C(F)(F)F)c1

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

Standard InChI Key:  ZOSMQYUVHWSYCZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
    3.8226  -17.8218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4856  -17.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2312  -16.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4140  -16.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597  -17.3439    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374  -16.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9343  -15.3346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226  -18.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9339  -15.9018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6466  -16.5577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879  -17.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1863  -18.5684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8933  -18.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8893  -19.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5954  -20.2051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3049  -19.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3039  -18.9764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5972  -18.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0109  -18.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7193  -18.9742    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0096  -17.7495    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7126  -18.1516    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
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4458056

   1-Methyl-3-oxidanyl-5-[[3-(trifluoromethyl)phenoxy]methyl]pyrazole-4-carboxylic acid

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: -1.14

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