2-((4-morpholinophenylamino)methyl)isoindoline-1,3-dione

ID: ALA1775068

PubChem CID: 2731384

Max Phase: Preclinical

Molecular Formula: C19H19N3O3

Molecular Weight: 337.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1c2ccccc2C(=O)N1CNc1ccc(N2CCOCC2)cc1

Standard InChI:  InChI=1S/C19H19N3O3/c23-18-16-3-1-2-4-17(16)19(24)22(18)13-20-14-5-7-15(8-6-14)21-9-11-25-12-10-21/h1-8,20H,9-13H2

Standard InChI Key:  NMFDNVJXDZBLQR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -4.4417   -0.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -0.8391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7291    0.8130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0141    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0092   -0.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2177   -0.6785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7333   -0.0036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2256    0.6653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754    1.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583   -1.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    0.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3244    0.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7388    0.0119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5626    0.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9715    0.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5506    1.4475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    1.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7938    0.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2100    0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    0.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4419    0.7480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0257    1.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1985    1.4586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5006    0.7181    0.0000 N   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
  9 10  2  0
  7 11  2  0
  8 12  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 16 19  1  0
 12 25  1  0
 13 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1775068

   N-(4-Morpholinoanilinomethyl)phthalimide

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: 337.38

Molecular Weight (Monoisotopic): 337.1426

AlogP: 2.19

#Rotatable Bonds: 4

Polar Surface Area: 61.88

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.48

CX LogP: 2.19

CX LogD: 2.19

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.87

Np Likeness Score: -1.44

References

1. Lu W, Liu X, Cao X, Xue M, Liu K, Zhao Z, Shen X, Jiang H, Xu Y, Huang J, Li H..  (2011)  SHAFTS: a hybrid approach for 3D molecular similarity calculation. 2. Prospective case study in the discovery of diverse p90 ribosomal S6 protein kinase 2 inhibitors to suppress cell migration.,  54  (10): [PMID:21488662] [10.1021/jm200139j]

2. Zhou W, Li S, Lu W, Yuan J, Xu Y, Li H, Huang J, Zhao Z.  (2016)  Isoindole-1,3-dione derivatives as RSK2 inhibitors: synthesis, molecular docking simulation and SAR analysis,  7  (2): [10.1039/C5MD00469A]

Source

Source(1):

• Scientific Literature