3-(4-morpholinylmethyl)-6-(3-phenyl-2-propenoyl)-2(3H)-benzoxazolone

ID: ALA249755

PubChem CID: 24744902

Max Phase: Preclinical

Molecular Formula: C21H20N2O4

Molecular Weight: 364.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1)c1ccc2c(c1)oc(=O)n2CN1CCOCC1

Standard InChI:  InChI=1S/C21H20N2O4/c24-19(9-6-16-4-2-1-3-5-16)17-7-8-18-20(14-17)27-21(25)23(18)15-22-10-12-26-13-11-22/h1-9,14H,10-13,15H2/b9-6+

Standard InChI Key:  AZCCVSYVUHAOTJ-RMKNXTFCSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   14.5527   -2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5516   -2.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2664   -3.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9828   -2.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9800   -2.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2646   -1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6980   -3.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4118   -2.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1269   -3.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8407   -2.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1282   -4.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5545   -3.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5469   -1.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8365   -2.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2670   -2.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2647   -2.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0482   -3.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5348   -2.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0519   -1.8021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.3598   -2.4727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3090   -1.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1164   -0.8489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6635   -1.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4679   -1.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7291   -0.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1796    0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3689   -0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 13  1  0
  1  2  2  0
 13 14  2  0
 14 10  1  0
 15 16  2  0
  4  7  1  0
  3  4  2  0
  7  8  2  0
  8  9  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
  4  5  1  0
 18 20  2  0
  9 10  1  0
 19 21  1  0
  2  3  1  0
 21 22  1  0
 22 23  1  0
  9 11  2  0
  5  6  2  0
 10 12  2  0
 12 16  1  0
  6  1  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA249755

   3-(morpholin-4-ylmethyl)-6-[(E)-3-phenylprop-2-enoyl]-1,3-benzoxazol-2-one

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: 364.40

Molecular Weight (Monoisotopic): 364.1423

AlogP: 2.78

#Rotatable Bonds: 5

Polar Surface Area: 64.68

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.07

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.21

References

1. Ivanova Y, Momekov G, Petrov O, Karaivanova M, Kalcheva V..  (2007)  Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones.,  42  (11): [PMID:17459529] [10.1016/j.ejmech.2007.02.019]

Source

Source(1):

• Scientific Literature