3-(3-Methoxyphenyl)-N,5-dimethyl-N-(6-(trifluoromethyl)pyridin-3-yl)isoxazole-4-carboxamide

ID: ALA3132969

PubChem CID: 76318386

Max Phase: Preclinical

Molecular Formula: C19H16F3N3O3

Molecular Weight: 391.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(-c2noc(C)c2C(=O)N(C)c2ccc(C(F)(F)F)nc2)c1

Standard InChI:  InChI=1S/C19H16F3N3O3/c1-11-16(17(24-28-11)12-5-4-6-14(9-12)27-3)18(26)25(2)13-7-8-15(23-10-13)19(20,21)22/h4-10H,1-3H3

Standard InChI Key:  QBWKNZQCZMOAPF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.8737   -9.4906    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6602  -10.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8363  -10.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5406   -9.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3870  -11.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7995  -11.7371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5620  -11.0226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3245  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1495  -11.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5620  -12.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1495  -13.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3245  -13.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9120  -12.4515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9120  -13.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3224  -14.6476    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.4995  -14.5950    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.0962  -13.9240    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7437   -9.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1495  -10.3081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1793  -10.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9942  -10.7996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5134  -11.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2177  -12.2110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4029  -12.3400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8837  -11.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3282  -11.3117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8474  -11.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
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  9 14  2  0
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  5 19  1  0
  8 20  1  0
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 21 26  2  0
 27 28  1  0
 23 27  1  0
  3 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3132969

   3-(3-methoxyphenyl)-N,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3-yl]-1,2-oxazole-4-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 391.35

Molecular Weight (Monoisotopic): 391.1144

AlogP: 4.35

#Rotatable Bonds: 4

Polar Surface Area: 68.46

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.72

CX LogP: 3.41

CX LogD: 3.41

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.66

Np Likeness Score: -1.75

References

1. Futatsugi K, Bahnck KB, Brenner MB, Buxton J, Chin JE, Coffey SB, Dubins J, Flynn D, Gautreau D, Guzman-Perez A, Hadcock JR, Hepworth D, Herr M, Hinchey T, Janssen AM, Jennings SM, Jiao W, Lavergne SY, Li B, Li M, Munchhof MJ, Orr STM, Piotrowski DW, Roush NS, Sammons M, Stevens BD, Storer G, Wang J, Warmus JS, Wei L, Wolford AC.  (2013)  Optimization of triazole-based TGR5 agonists towards orally available agents,  4  (1): [10.1039/C2MD20174G]

Source

Source(1):

• Scientific Literature