N-(2,2-diphenylethyl)-4-hydroxy-1,2,5-oxadiazole-3-carboxamide

ID: ALA4464362

PubChem CID: 155530572

Max Phase: Preclinical

Molecular Formula: C17H15N3O3

Molecular Weight: 309.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCC(c1ccccc1)c1ccccc1)c1nonc1O

Standard InChI:  InChI=1S/C17H15N3O3/c21-16(15-17(22)20-23-19-15)18-11-14(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14H,11H2,(H,18,21)(H,20,22)

Standard InChI Key:  SFWSCQSOJOPJMO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   18.8292   -5.5227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4922   -5.0448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2378   -4.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4206   -4.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1663   -5.0448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9440   -3.8527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6532   -4.2586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9409   -3.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3594   -3.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0686   -4.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0717   -5.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7748   -3.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3655   -5.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3682   -6.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0780   -6.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7865   -6.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7803   -5.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4800   -4.2497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1857   -3.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1831   -3.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4689   -2.6153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7661   -3.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9405   -3.6026    0.0000 O   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  1  0
  6  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 11  1  0
 12 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 12  1  0
  4 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4464362

   ---

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: 309.33

Molecular Weight (Monoisotopic): 309.1113

AlogP: 2.34

#Rotatable Bonds: 5

Polar Surface Area: 88.25

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.38

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 1.62

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -0.92

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