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

ID: ALA4569109

PubChem CID: 155550546

Max Phase: Preclinical

Molecular Formula: C16H18N2O4

Molecular Weight: 302.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cn1nc(OCC2CC2)c(C(=O)O)c1COc1ccccc1

Standard InChI:  InChI=1S/C16H18N2O4/c1-18-13(10-21-12-5-3-2-4-6-12)14(16(19)20)15(17-18)22-9-11-7-8-11/h2-6,11H,7-10H2,1H3,(H,19,20)

Standard InChI Key:  CRZPSCCTCRYCQI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   32.1148  -18.1974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.7777  -17.7195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5234  -16.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7062  -16.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4518  -17.7195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2295  -16.5274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2264  -15.7102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.1148  -19.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2261  -16.2773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.9388  -16.9333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4801  -18.1268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4785  -18.9440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.1854  -19.3539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1815  -20.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8876  -20.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5971  -20.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5960  -19.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8893  -18.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4053  -16.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0034  -15.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0085  -14.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2969  -15.1455    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
  9 19  1  0
 19 20  1  0
 21 20  1  0
 22 21  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4569109

   ---

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: 302.33

Molecular Weight (Monoisotopic): 302.1267

AlogP: 2.49

#Rotatable Bonds: 7

Polar Surface Area: 73.58

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.02

CX Basic pKa: ┄

CX LogP: 2.76

CX LogD: -0.38

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.85

Np Likeness Score: -0.82

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