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

ID: ALA5169488

PubChem CID: 168269340

Max Phase: Preclinical

Molecular Formula: C19H20N2O3

Molecular Weight: 324.38

Names and Identifiers

Canonical SMILES:  Nc1ccc(CC2OC(=O)c3cc(N4CC[C@@H](O)C4)ccc32)cc1

Standard InChI:  InChI=1S/C19H20N2O3/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,7-9,11,20H2/t15-,18?/m1/s1

Standard InChI Key:  VMCCHQZHAUPELO-NNJIEVJOSA-N

Molfile:  

 
     RDKit          2D

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   -1.4278    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
    0.0010    0.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010   -0.7939    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
    1.2706   -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    1.0707    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
    2.1025    2.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9095    2.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4616    1.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2686    1.7568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2067    0.8006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3997    0.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0406   -1.8335    0.0000 O   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
   -1.4278   -0.7939    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
   -2.2286   -2.0269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0356   -2.1984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4481   -1.4839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2686   -1.3977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -0.8708    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
 12 11  2  0
 12 13  1  0
 14 12  1  0
 15 14  2  0
  9 15  1  0
  5 16  2  0
 17  4  1  0
 18 17  2  0
  1 18  1  0
 19 18  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5169488

   ---

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: 324.38

Molecular Weight (Monoisotopic): 324.1474

AlogP: 2.29

#Rotatable Bonds: 3

Polar Surface Area: 75.79

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.17

CX LogP: 2.14

CX LogD: 2.14

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.67

Np Likeness Score: 0.26

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