3-(3,4-difluorobenzyl)-6-((R)-3-methoxypyrrolidin-1-yl)isobenzofuran-1(3H)-one

ID: ALA5187602

PubChem CID: 168281887

Max Phase: Preclinical

Molecular Formula: C20H19F2NO3

Molecular Weight: 359.37

Names and Identifiers

Canonical SMILES:  CO[C@@H]1CCN(c2ccc3c(c2)C(=O)OC3Cc2ccc(F)c(F)c2)C1

Standard InChI:  InChI=1S/C20H19F2NO3/c1-25-14-6-7-23(11-14)13-3-4-15-16(10-13)20(24)26-19(15)9-12-2-5-17(21)18(22)8-12/h2-5,8,10,14,19H,6-7,9,11H2,1H3/t14-,19?/m1/s1

Standard InChI Key:  NORVIURVSAMEOB-MJTSIZKDSA-N

Molfile:  

 
     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -1.1853   -0.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    0.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -0.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2435   -1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282   -1.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5131   -0.7736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0282   -0.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2831    0.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0901    0.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3450    1.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1520    1.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070    2.5907    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7041    1.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5111    1.3645    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4492    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6422    0.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2831   -2.2257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709   -1.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1853   -1.1862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8999   -1.5986    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -2.4192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7930   -2.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2056   -1.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0261   -1.7900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5111   -2.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -1.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  4  5  1  0
  6  5  1  0
  3  7  1  0
  7  6  1  0
  7  8  1  0
  8  9  1  0
 10  9  2  0
 11 10  1  0
 11 12  1  0
 13 11  2  0
 13 14  1  0
 15 13  1  0
 16 15  2  0
  9 16  1  0
  5 17  2  0
 18  4  1  0
 19 18  2  0
  1 19  1  0
 20 19  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  1
 24 25  1  0
 23 26  1  0
 26 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5187602

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 359.37

Molecular Weight (Monoisotopic): 359.1333

AlogP: 3.64

#Rotatable Bonds: 4

Polar Surface Area: 38.77

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 14.00

CX Basic pKa: 1.14

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: -0.48

References

1. Liu K, Zhou S, Zhou J, Bo R, Wang X, Xu T, Yuan Y, Xu B..  (2022)  Discovery of 3, 6-disubstituted isobenzofuran-1(3H)-ones as novel inhibitors of monoamine oxidases.,  67  [PMID:35472505] [10.1016/j.bmcl.2022.128748]

Source

Source(1):

• Scientific Literature