(S)-Ethyl 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate

ID: ALA3580850

PubChem CID: 830179

Max Phase: Preclinical

Molecular Formula: C19H17NO4

Molecular Weight: 323.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@H](Cc1ccccc1)N1C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C19H17NO4/c1-2-24-19(23)16(12-13-8-4-3-5-9-13)20-17(21)14-10-6-7-11-15(14)18(20)22/h3-11,16H,2,12H2,1H3/t16-/m0/s1

Standard InChI Key:  DYGUJTAGRHYCOM-INIZCTEOSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0825    2.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0907   -2.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8212    1.3487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3219    1.3685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2078    2.3801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8569   -1.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0559    2.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2558    2.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3575   -1.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1287   -2.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6285   -2.4897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3572   -1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5862    0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0864    0.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  8 10  1  0
  9 11  2  0
  7 12  2  0
 10 13  1  0
 13 14  1  0
 13 15  2  0
 10 16  1  6
 14 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3580850

   ethyl (2S)-2-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 323.35

Molecular Weight (Monoisotopic): 323.1158

AlogP: 2.46

#Rotatable Bonds: 5

Polar Surface Area: 63.68

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.12

CX LogD: 3.12

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.66

References

1. Coelho LCD, Cardoso MVdO, Moreira DRM, Gomes PATdM, Cavalcanti SMT, Oliveira AR, Filho GBdO, Siqueira LRPd, Barbosa MdO, Borba EFdO, Silva TGd, Kaskow B, Karimi M, Abraham LJ, Leite ACL.  (2014)  Novel phthalimide derivatives with TNF- and IL-1 expression inhibitory and apoptotic inducing properties,  5  (6): [10.1039/C4MD00070F]

Source

Source(1):

• Scientific Literature