methyl ethyl(2-(5-(trifluoromethyl)pyridin-3-yl)benzo[d]oxazol-6-yl)phosphinate

ID: ALA4756278

PubChem CID: 162655210

Max Phase: Preclinical

Molecular Formula: C16H14F3N2O3P

Molecular Weight: 370.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3cncc(C(F)(F)F)c3)oc2c1

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

Standard InChI Key:  ZKWZJXRENRSUAZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.9462  -12.8934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9451  -13.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6531  -14.1219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6514  -12.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3600  -12.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3648  -13.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1448  -13.9569    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.6222  -13.2918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1371  -12.6324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.4374  -13.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8495  -13.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6659  -13.9889    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8390  -12.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2384  -12.4850    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   32.2382  -11.6678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5308  -12.8938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8230  -12.4853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2337  -13.3021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5236  -13.7065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6540  -12.5706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0672  -13.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0575  -11.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8746  -11.8540    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.6437  -11.1553    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.4616  -11.1476    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 21  2  0
 20 13  2  0
 13 10  1  0
  8 10  1  0
  1 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4756278

   ---

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: 2.71

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -1.26

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