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

ID: ALA4514633

PubChem CID: 155539488

Max Phase: Preclinical

Molecular Formula: C12H12N2O3S

Molecular Weight: 264.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1nc(O)c(C(=O)O)c1CSc1ccccc1

Standard InChI:  InChI=1S/C12H12N2O3S/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:  ZHAYGNAAJUYMAL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
   39.1187  -10.6157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.7816  -10.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5273   -9.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7101   -9.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4557  -10.1378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2334   -8.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2304   -8.1285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.1187  -11.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2300   -8.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.9427   -9.3516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.4840  -10.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.4824  -11.3623    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.1893  -11.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.1854  -12.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8915  -12.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6010  -12.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.5999  -11.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8933  -11.3641    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:

   

   ALA4514633

   ---

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: 264.31

Molecular Weight (Monoisotopic): 264.0569

AlogP: 2.12

#Rotatable Bonds: 4

Polar Surface Area: 75.35

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.07

CX Basic pKa: 0.01

CX LogP: 3.01

CX LogD: -1.83

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: -1.01

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