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

ID: ALA4792864

PubChem CID: 162670757

Max Phase: Preclinical

Molecular Formula: C17H14F2NO5P

Molecular Weight: 381.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3ccc4c(c3)OC(F)(F)O4)nc2c1

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

Standard InChI Key:  JYIAJAYOAICDAZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   18.8284  -18.3703    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.4239  -19.0802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2410  -19.0755    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4257  -19.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4245  -20.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1326  -20.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1308  -19.2862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8394  -19.6915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8442  -20.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6242  -20.7586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1016  -20.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6165  -19.4340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7165  -20.9227    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.0091  -20.5135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7158  -21.7399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0078  -22.1479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2909  -21.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0782  -22.2878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9168  -20.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3289  -20.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1454  -20.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3184  -19.3803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1334  -19.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5505  -20.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3505  -19.8992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6756  -18.7577    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
  5 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 13 17  1  0
 17 18  1  0
 19 20  2  0
 20 21  1  0
 21 24  2  0
 23 22  2  0
 22 19  1  0
 11 19  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:

   

   ALA4792864

   ---

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: -0.86

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