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

ID: ALA4457827

PubChem CID: 155525976

Max Phase: Preclinical

Molecular Formula: C12H12N2O4

Molecular Weight: 248.24

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1nc(O)c(C(=O)O)c1COc1ccccc1

Standard InChI:  InChI=1S/C12H12N2O4/c1-14-9(10(12(16)17)11(15)13-14)7-18-8-5-3-2-4-6-8/h2-6H,7H2,1H3,(H,13,15)(H,16,17)

Standard InChI Key:  DYMIFCDYKKQDNF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   19.8817  -11.0697    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5446  -10.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2903   -9.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4731   -9.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2187  -10.5918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9964   -9.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9933   -8.5825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8817  -11.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9930   -9.1496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7057   -9.8056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2470  -10.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2454  -11.8163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9523  -12.2262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9484  -13.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6545  -13.4530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3640  -13.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3629  -12.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6562  -11.8181    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:

   

   ALA4457827

   ---

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: 248.24

Molecular Weight (Monoisotopic): 248.0797

AlogP: 1.40

#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: 2.49

CX LogD: -2.39

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.85

Np Likeness Score: -0.72

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