3-(5-Fluoro-2-methylbenzyl)-6-((R)-3-hydroxypyrrolidin-1-yl)isobenzofuran-1(3H)-one

ID: ALA5196664

PubChem CID: 168285945

Max Phase: Preclinical

Molecular Formula: C20H20FNO3

Molecular Weight: 341.38

Names and Identifiers

Canonical SMILES:  Cc1ccc(F)cc1CC1OC(=O)c2cc(N3CC[C@@H](O)C3)ccc21

Standard InChI:  InChI=1S/C20H20FNO3/c1-12-2-3-14(21)8-13(12)9-19-17-5-4-15(10-18(17)20(24)25-19)22-7-6-16(23)11-22/h2-5,8,10,16,19,23H,6-7,9,11H2,1H3/t16-,19?/m1/s1

Standard InChI Key:  SWDIUHBIIMOIGU-VTBWFHPJSA-N

Molfile:  

 
     RDKit          2D

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   -1.1729   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -1.4271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -1.7047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0136   -1.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7806   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9736   -2.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584   -1.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406   -1.2696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956   -2.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255   -0.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406    0.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2956    0.8499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    0.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136   -0.0332    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.7164    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1644    1.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3574    1.8060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054    2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2560   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584    0.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  5  6  1  1
  7  5  1  0
  8  7  1  0
  3  8  1  0
  2  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 13 11  1  0
 14 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 16  2  0
 22 23  1  0
 24 14  1  0
 10 24  2  0
 24 25  1  0
 25  1  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5196664

   ---

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: 341.38

Molecular Weight (Monoisotopic): 341.1427

AlogP: 3.16

#Rotatable Bonds: 3

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.94

CX Basic pKa: 1.12

CX LogP: 3.62

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -0.43

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