3-(4-(2-hydroxyethyl)phenylamino)-1-(4-propoxyphenyl)pyrrolidine-2,5-dione

ID: ALA3736205

Cas Number: 342406-05-7

PubChem CID: 2936770

Max Phase: Preclinical

Molecular Formula: C21H24N2O4

Molecular Weight: 368.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCOc1ccc(N2C(=O)CC(Nc3ccc(CCO)cc3)C2=O)cc1

Standard InChI:  InChI=1S/C21H24N2O4/c1-2-13-27-18-9-7-17(8-10-18)23-20(25)14-19(21(23)26)22-16-5-3-15(4-6-16)11-12-24/h3-10,19,22,24H,2,11-14H2,1H3

Standard InChI Key:  AJDMSARFYPOETQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6331   -3.6060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2526    1.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2524    0.2436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4979   -1.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0317   -0.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9821   -2.1508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4992    2.5362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7454    0.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4584    1.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9579    1.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7413    0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0252   -0.8490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5257   -0.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2417    0.5049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0237   -0.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.5241   -0.7403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1494   -1.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
 14 16  2  0
 12 17  2  0
 13 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3736205

   3-{[4-(2-Hydroxyethyl)phenyl]amino}-1-(4-propoxyphenyl)pyrrolidine-2,5-dione

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: 368.43

Molecular Weight (Monoisotopic): 368.1736

AlogP: 2.75

#Rotatable Bonds: 8

Polar Surface Area: 78.87

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.78

CX Basic pKa: 2.25

CX LogP: 2.38

CX LogD: 2.38

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.88

References

1. Wang X, Sun C, Fang L, Yin D.  (2015)  Discovery of novel sphingosine kinase 1 inhibitors via structure-based hierarchical virtual screening,  6  (3): [10.1039/C4MD00312H]

Source

Source(1):

• Scientific Literature