Ethyl 3-hydroxy-1-methyl-5-(phenoxymethyl)-1H-pyrazole-4-carboxylate

ID: ALA4440085

PubChem CID: 155514549

Max Phase: Preclinical

Molecular Formula: C14H16N2O4

Molecular Weight: 276.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1c(O)nn(C)c1COc1ccccc1

Standard InChI:  InChI=1S/C14H16N2O4/c1-3-19-14(18)12-11(16(2)15-13(12)17)9-20-10-7-5-4-6-8-10/h4-8H,3,9H2,1-2H3,(H,15,17)

Standard InChI Key:  RQENMQYFVZAYEG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   17.5291  -17.4462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1921  -16.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9377  -16.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1205  -16.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8662  -16.9683    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6439  -15.7762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6408  -14.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5291  -18.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6405  -15.5262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3531  -16.1821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8945  -17.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8929  -18.1928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5998  -18.6028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5959  -19.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3020  -19.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0114  -19.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0104  -18.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3037  -18.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0593  -15.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7686  -16.1768    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
 10 19  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4440085

   ---

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: 276.29

Molecular Weight (Monoisotopic): 276.1110

AlogP: 1.88

#Rotatable Bonds: 5

Polar Surface Area: 73.58

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.79

CX Basic pKa: ┄

CX LogP: 3.19

CX LogD: 2.52

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.84

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