methyl (2-(2-(difluoromethoxy)pyridin-4-yl)benzo[d]oxazol-5-yl)(ethyl)phosphinate

ID: ALA4796139

PubChem CID: 162674258

Max Phase: Preclinical

Molecular Formula: C16H15F2N2O4P

Molecular Weight: 368.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3ccnc(OC(F)F)c3)nc2c1

Standard InChI:  InChI=1S/C16H15F2N2O4P/c1-3-25(21,22-2)11-4-5-13-12(9-11)20-15(23-13)10-6-7-19-14(8-10)24-16(17)18/h4-9,16H,3H2,1-2H3

Standard InChI Key:  XWLQZIWKAASSDY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   22.5952   -2.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5940   -3.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3021   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3003   -2.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0089   -2.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0137   -3.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7937   -4.0557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2711   -3.3905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7860   -2.7312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8860   -4.2198    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.1786   -3.8106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8853   -5.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1773   -5.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4604   -4.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2477   -5.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0863   -3.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4984   -4.0921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3149   -4.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7201   -3.3770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3029   -2.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4879   -2.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7048   -1.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5220   -1.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9239   -1.2459    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.9357   -2.6549    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
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 16  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4796139

   ---

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: 368.28

Molecular Weight (Monoisotopic): 368.0738

AlogP: 4.06

#Rotatable Bonds: 6

Polar Surface Area: 74.45

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.06

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -1.25

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