3-(4-Fluorobenzyl)-6-((R)-3-hydroxypyrrolidin-1-yl)isobenzofuran-1(3H)-one

ID: ALA5197093

PubChem CID: 168289290

Max Phase: Preclinical

Molecular Formula: C19H18FNO3

Molecular Weight: 327.36

Names and Identifiers

Canonical SMILES:  O=C1OC(Cc2ccc(F)cc2)c2ccc(N3CC[C@@H](O)C3)cc21

Standard InChI:  InChI=1S/C19H18FNO3/c20-13-3-1-12(2-4-13)9-18-16-6-5-14(10-17(16)19(23)24-18)21-8-7-15(22)11-21/h1-6,10,15,18,22H,7-9,11H2/t15-,18?/m1/s1

Standard InChI Key:  FSYNERMVWCRCGM-NNJIEVJOSA-N

Molfile:  

 
     RDKit          2D

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   -1.4278   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1423   -1.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -0.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4480   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2685   -1.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0355   -2.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2286   -2.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857   -1.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406   -1.8334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2706   -0.3813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7857    0.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406    1.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476    1.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3996    0.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2066    0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4615    1.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2685    1.7568    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    2.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025    2.0268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7134    0.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA5197093

   ---

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: 327.36

Molecular Weight (Monoisotopic): 327.1271

AlogP: 2.85

#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: 13.98

CX Basic pKa: 1.12

CX LogP: 3.11

CX LogD: 3.11

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.88

Np Likeness Score: -0.11

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