methyl (2-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)benzo[d]oxazol-6-yl)(ethyl)phosphinate

ID: ALA4740118

PubChem CID: 162644796

Max Phase: Preclinical

Molecular Formula: C17H14F2NO5P

Molecular Weight: 381.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3ccc4c(c3)OC(F)(F)O4)oc2c1

Standard InChI:  InChI=1S/C17H14F2NO5P/c1-3-26(21,22-2)11-5-6-12-14(9-11)23-16(20-12)10-4-7-13-15(8-10)25-17(18,19)24-13/h4-9H,3H2,1-2H3

Standard InChI Key:  RIDIGEKKTGRJGX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   39.1880   -2.0884    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.6102   -2.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4031   -2.8797    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.6078   -3.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6067   -4.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3147   -4.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3129   -2.8681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0215   -3.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0263   -4.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8064   -4.3404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2837   -3.6753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7986   -3.0159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0989   -3.6700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5111   -4.3769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3275   -4.3725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.5005   -2.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9000   -2.8686    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   31.8998   -2.0514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1924   -3.2773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4846   -2.8689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8952   -3.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1851   -4.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3156   -2.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7288   -3.6620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5297   -3.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8611   -2.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12  8  1  0
 13 14  2  0
 14 15  1  0
 15 24  2  0
 23 16  2  0
 16 13  1  0
 11 13  1  0
  4 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 23 24  1  0
 24 25  1  0
 25  2  1  0
  2 26  1  0
 26 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740118

   ---

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: 381.27

Molecular Weight (Monoisotopic): 381.0578

AlogP: 4.39

#Rotatable Bonds: 4

Polar Surface Area: 70.79

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.62

Np Likeness Score: -0.92

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