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

ID: ALA436836

PubChem CID: 24745062

Max Phase: Preclinical

Molecular Formula: C22H22N2O5

Molecular Weight: 394.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)c2ccc3c(c2)oc(=O)n3CN2CCOCC2)cc1

Standard InChI:  InChI=1S/C22H22N2O5/c1-27-18-6-2-16(3-7-18)4-9-20(25)17-5-8-19-21(14-17)29-22(26)24(19)15-23-10-12-28-13-11-23/h2-9,14H,10-13,15H2,1H3/b9-4+

Standard InChI Key:  LXPQREMCGLTAIS-RUDMXATFSA-N

Molfile:  

     RDKit          2D

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   16.1277  -14.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1266  -14.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8414  -15.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5578  -14.8894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5550  -14.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8396  -13.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2730  -15.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9868  -14.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7019  -15.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4157  -14.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7032  -16.1235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1295  -15.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1219  -13.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4115  -14.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8420  -14.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8397  -14.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6232  -15.1403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1098  -14.4746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6269  -13.8062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9348  -14.4768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4132  -13.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4130  -12.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8840  -13.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6914  -12.8530    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2355  -13.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0398  -13.3035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3011  -12.5205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7516  -11.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9408  -12.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1 21  1  0
  2  3  1  0
 21 22  1  0
  9 11  2  0
 19 23  1  0
  5  6  2  0
 23 24  1  0
 24 25  1  0
 10 12  2  0
 12 16  1  0
  6  1  1  0
 15 13  1  0
  1  2  2  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA436836

   6-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-3-(morpholin-4-ylmethyl)-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: 394.43

Molecular Weight (Monoisotopic): 394.1529

AlogP: 2.79

#Rotatable Bonds: 6

Polar Surface Area: 73.91

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.07

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: -1.13

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