methyl (2-(3-(difluoromethoxy)phenyl)benzo[d]oxazol-6-yl)(ethyl)phosphinate

ID: ALA4791976

PubChem CID: 162670572

Max Phase: Preclinical

Molecular Formula: C17H16F2NO4P

Molecular Weight: 367.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3cccc(OC(F)F)c3)oc2c1

Standard InChI:  InChI=1S/C17H16F2NO4P/c1-3-25(21,22-2)13-7-8-14-15(10-13)24-16(20-14)11-5-4-6-12(9-11)23-17(18)19/h4-10,17H,3H2,1-2H3

Standard InChI Key:  UGAHEHWDWCWEAW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   15.3821  -19.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3810  -20.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0958  -21.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0940  -19.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8094  -19.8716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8142  -20.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6018  -20.9489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0836  -20.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5939  -19.6117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9066  -20.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3228  -20.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1470  -20.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3121  -19.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1350  -19.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5521  -20.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6675  -19.4629    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.6673  -18.6379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9532  -19.8756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2386  -19.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6627  -20.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9458  -20.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5422  -18.8319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3673  -18.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7745  -18.1085    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.7849  -19.5374    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
  1 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791976

   ---

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: 367.29

Molecular Weight (Monoisotopic): 367.0785

AlogP: 4.67

#Rotatable Bonds: 6

Polar Surface Area: 61.56

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.05

CX LogD: 4.05

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -1.46

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