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

ID: ALA4544292

PubChem CID: 155552909

Max Phase: Preclinical

Molecular Formula: C14H16N2O4

Molecular Weight: 276.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOc1nn(C)c(COc2ccccc2)c1C(=O)O

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

Standard InChI Key:  FTKLMHXRXQTCDL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   25.1439  -17.6031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8068  -17.1252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5525  -16.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7353  -16.3443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4809  -17.1252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2586  -15.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2556  -15.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1439  -18.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2552  -15.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9679  -16.3390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5092  -17.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5076  -18.3497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2145  -18.7596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2106  -19.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9167  -19.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6262  -19.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6251  -18.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9185  -18.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4344  -15.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0325  -14.9637    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
M  END

Alternative Forms

1. Parent:

   

   ALA4544292

   ---

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: 2.10

#Rotatable Bonds: 6

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: 2.34

CX LogD: -0.81

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.87

Np Likeness Score: -0.98

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