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

ID: ALA4514989

PubChem CID: 155539527

Max Phase: Preclinical

Molecular Formula: C12H13N3O3

Molecular Weight: 247.25

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1nc(O)c(C(=O)O)c1CNc1ccccc1

Standard InChI:  InChI=1S/C12H13N3O3/c1-15-9(10(12(17)18)11(16)14-15)7-13-8-5-3-2-4-6-8/h2-6,13H,7H2,1H3,(H,14,16)(H,17,18)

Standard InChI Key:  YXURSAIUJSPFDO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   25.7919  -10.5826    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4548  -10.1047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2004   -9.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3833   -9.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1289  -10.1047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9066   -8.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9035   -8.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7919  -11.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9032   -8.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.6159   -9.3186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1572  -10.5121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1556  -11.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8625  -11.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8586  -12.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5647  -12.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2741  -12.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2731  -11.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5664  -11.3311    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
  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
M  END

Alternative Forms

1. Parent:

   

   ALA4514989

   ---

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: 247.25

Molecular Weight (Monoisotopic): 247.0957

AlogP: 1.44

#Rotatable Bonds: 4

Polar Surface Area: 87.38

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.86

CX Basic pKa: 3.56

CX LogP: 1.34

CX LogD: -2.74

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.76

Np Likeness Score: -0.90

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