3-(2,5-Difluorobenzyl)-6-((R)-3-hydroxypyrrolidin-1-yl)isobenzofuran-1(3H)-one

ID: ALA5200168

PubChem CID: 168292365

Max Phase: Preclinical

Molecular Formula: C19H17F2NO3

Molecular Weight: 345.35

Names and Identifiers

Canonical SMILES:  O=C1OC(Cc2cc(F)ccc2F)c2ccc(N3CC[C@@H](O)C3)cc21

Standard InChI:  InChI=1S/C19H17F2NO3/c20-12-1-4-17(21)11(7-12)8-18-15-3-2-13(9-16(15)19(24)25-18)22-6-5-14(23)10-22/h1-4,7,9,14,18,23H,5-6,8,10H2/t14-,18?/m1/s1

Standard InChI Key:  OUTDHZYYTZKKEI-IKJXHCRLSA-N

Molfile:  

 
     RDKit          2D

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   -0.4584    0.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -0.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405   -1.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5254   -0.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405    0.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2955    0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1024    1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3573    1.8059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8053    2.4190    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.1642    1.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7162    1.3644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4613    0.5798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0133   -0.0332    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.6544    0.4082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2955   -2.0541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4584   -1.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8873   -1.4270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9735   -2.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7805   -2.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929   -1.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0133   -1.6183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6409   -1.0915    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
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 12 10  1  0
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  9 16  1  0
  5 17  2  0
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 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
 23 25  1  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5200168

   ---

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: 345.35

Molecular Weight (Monoisotopic): 345.1176

AlogP: 2.99

#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: 13.77

CX Basic pKa: 1.12

CX LogP: 3.25

CX LogD: 3.25

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -0.57

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