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

ID: ALA4742288

PubChem CID: 162646126

Max Phase: Preclinical

Molecular Formula: C16H15F2N2O3P

Molecular Weight: 352.28

Molecule Type: Unknown

Names and Identifiers

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

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

Standard InChI Key:  NGADHVSEDGXSMG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   33.6603  -19.0141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6591  -19.8336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3672  -20.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3654  -18.6052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0740  -19.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0788  -19.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8588  -20.0776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.3362  -19.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8511  -18.7531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1514  -19.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5635  -20.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3800  -20.1096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.5530  -18.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9525  -18.6057    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   32.9523  -17.7885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2448  -19.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5370  -18.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9477  -19.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2376  -19.8272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3680  -18.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7812  -19.3991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7715  -17.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5886  -17.9747    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.3577  -17.2759    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
M  END

Alternative Forms

1. Parent:

   

   ALA4742288

   ---

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: -1.22

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