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

ID: ALA4759170

PubChem CID: 162658488

Max Phase: Preclinical

Molecular Formula: C16H15F2N2O3P

Molecular Weight: 352.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3cncc(C(F)F)c3)nc2c1

Standard InChI:  InChI=1S/C16H15F2N2O3P/c1-3-24(21,22-2)12-4-5-14-13(7-12)20-16(23-14)11-6-10(15(17)18)8-19-9-11/h4-9,15H,3H2,1-2H3

Standard InChI Key:  VNJVSYDFARJCBK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   22.0999  -14.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0987  -15.0419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8068  -15.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8050  -13.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5136  -14.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5184  -15.0374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2984  -15.2859    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7758  -14.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2907  -13.9613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5910  -14.6154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0032  -15.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8196  -15.3179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.2248  -14.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8077  -13.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9926  -13.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2096  -13.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0267  -13.1804    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.7943  -12.4843    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.3907  -15.4500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.6833  -15.0408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3901  -16.2672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6820  -16.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9651  -16.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7548  -15.8157    0.0000 C   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 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
  2 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759170

   ---

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: 352.28

Molecular Weight (Monoisotopic): 352.0788

AlogP: 4.40

#Rotatable Bonds: 5

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: 3.01

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.64

Np Likeness Score: -1.16

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