methyl ethyl(2-(4-methoxyphenyl)benzo[d]oxazol-5-yl)phosphinate

ID: ALA4755690

PubChem CID: 162655509

Max Phase: Preclinical

Molecular Formula: C17H18NO4P

Molecular Weight: 331.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3ccc(OC)cc3)nc2c1

Standard InChI:  InChI=1S/C17H18NO4P/c1-4-23(19,21-3)14-9-10-16-15(11-14)18-17(22-16)12-5-7-13(20-2)8-6-12/h5-11H,4H2,1-3H3

Standard InChI Key:  XOPDITAIBZYEDC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    3.9485   -8.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9474   -9.5439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6622   -9.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604   -8.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3757   -8.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3806   -9.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1681   -9.7902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6500   -9.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1602   -8.4530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4729   -9.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8891   -9.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7133   -9.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8784   -8.3987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7013   -8.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1184   -9.1053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2326   -9.9558    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5184   -9.5427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320  -10.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171  -11.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417  -10.3665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9405  -11.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9433   -9.0993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3609   -9.8108    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 15  2  0
 14 13  2  0
 13 10  1  0
  8 10  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4755690

   ---

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: 331.31

Molecular Weight (Monoisotopic): 331.0973

AlogP: 4.07

#Rotatable Bonds: 5

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: 3.20

CX LogD: 3.20

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.66

Np Likeness Score: -0.81

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