3-Hydroxy-1-methyl-5-((methyl(phenyl)amino)methyl)-1H-pyrazole-4-carboxylic acid

ID: ALA4451149

PubChem CID: 155522278

Max Phase: Preclinical

Molecular Formula: C13H15N3O3

Molecular Weight: 261.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(Cc1c(C(=O)O)c(O)nn1C)c1ccccc1

Standard InChI:  InChI=1S/C13H15N3O3/c1-15(9-6-4-3-5-7-9)8-10-11(13(18)19)12(17)14-16(10)2/h3-7H,8H2,1-2H3,(H,14,17)(H,18,19)

Standard InChI Key:  WKFNJMDGGOCESI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   31.8630  -10.6941    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.5260  -10.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2716   -9.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4544   -9.4353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2000  -10.2162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.9778   -9.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9747   -8.2069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9743   -8.7740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.6870   -9.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3028  -10.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4715  -11.2694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.2483  -11.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8634  -11.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8630  -11.5113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4132  -12.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1892  -12.5743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7982  -12.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6260  -11.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8503  -10.9749    0.0000 C   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
  4  8  1  0
  6  9  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  1 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4451149

   ---

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: 261.28

Molecular Weight (Monoisotopic): 261.1113

AlogP: 1.46

#Rotatable Bonds: 4

Polar Surface Area: 78.59

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.07

CX Basic pKa: 1.45

CX LogP: 2.60

CX LogD: -2.10

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.87

Np Likeness Score: -1.03

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