methyl ethyl(2-(2-(trifluoromethyl)pyridin-3-yl)benzo[d]oxazol-5-yl)phosphinate

ID: ALA4785130

PubChem CID: 162665814

Max Phase: Preclinical

Molecular Formula: C16H14F3N2O3P

Molecular Weight: 370.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3cccnc3C(F)(F)F)nc2c1

Standard InChI:  InChI=1S/C16H14F3N2O3P/c1-3-25(22,23-2)10-6-7-13-12(9-10)21-15(24-13)11-5-4-8-20-14(11)16(17,18)19/h4-9H,3H2,1-2H3

Standard InChI Key:  KBIIESRQDBPGLI-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   15.8400   -2.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8389   -3.5148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5537   -3.9276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5519   -2.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2672   -2.6838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2721   -3.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0596   -3.7611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5415   -3.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0518   -2.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3645   -3.0842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7806   -3.7979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6048   -3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7699   -2.3696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5928   -2.3615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.0099   -3.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1241   -3.9267    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.4099   -3.5136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1235   -4.7517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4087   -5.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8332   -4.3374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8320   -5.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3512   -1.6587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7576   -0.9407    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.5263   -1.6658    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.9331   -0.9417    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 14 13  2  0
 13 10  1  0
  8 10  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 13 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4785130

   ---

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: 370.27

Molecular Weight (Monoisotopic): 370.0694

AlogP: 4.48

#Rotatable Bonds: 4

Polar Surface Area: 65.22

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.12

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -1.06

References

1. Chatzopoulou M,Emer E,Lecci C,Rowley JA,Casagrande AS,Moir L,Squire SE,Davies SG,Harriman S,Wynne GM,Wilson FX,Davies KE,Russell AJ.  (2020)  Decreasing HepG2 Cytotoxicity by Lowering the Lipophilicity of Benzo[d]oxazolephosphinate Ester Utrophin Modulators.,  11  (12): [PMID:33335663] [10.1021/acsmedchemlett.0c00405]

2. Chatzopoulou, Maria and 16 more authors.  2020-03-12  Isolation, Structural Identification, Synthesis, and Pharmacological Profiling of 1,2-trans-Dihydro-1,2-diol Metabolites of the Utrophin Modulator Ezutromid.  [PMID:31599580]

3. Babbs, Arran and 19 more authors.  2020-07-23  2-Arylbenzo[d]oxazole Phosphinate Esters as Second-Generation Modulators of Utrophin for the Treatment of Duchenne Muscular Dystrophy.  [PMID:32551645]

4. Chatzopoulou, Maria and 12 more authors.  2020-12-10  Decreasing HepG2 Cytotoxicity by Lowering the Lipophilicity of Benzo[d]oxazolephosphinate Ester Utrophin Modulators.  [PMID:33335663]

Source

Source(1):

• Scientific Literature