6-(3-phenyl-2-propenoyl)-3-(1-piperidinylmethyl)-2(3H)-benzoxazolone

ID: ALA400946

PubChem CID: 24745065

Max Phase: Preclinical

Molecular Formula: C22H22N2O3

Molecular Weight: 362.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1)c1ccc2c(c1)oc(=O)n2CN1CCCCC1

Standard InChI:  InChI=1S/C22H22N2O3/c25-20(12-9-17-7-3-1-4-8-17)18-10-11-19-21(15-18)27-22(26)24(19)16-23-13-5-2-6-14-23/h1,3-4,7-12,15H,2,5-6,13-14,16H2/b12-9+

Standard InChI Key:  NQKLQOKSOHDASB-FMIVXFBMSA-N

Molfile:  

     RDKit          2D

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    4.1474   -3.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8622   -3.7569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787   -3.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5758   -2.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8604   -2.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2938   -3.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0076   -3.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7227   -3.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4365   -3.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7240   -4.5777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1504   -3.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1427   -2.1018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4323   -2.5170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8628   -2.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8606   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6440   -3.5945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1306   -2.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6477   -2.2604    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9556   -2.9310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9048   -1.4765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7123   -1.3072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2594   -1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0637   -1.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3250   -0.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7755   -0.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9647   -0.5277    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:

   

   ALA400946

   6-[(E)-3-phenylprop-2-enoyl]-3-(piperidin-1-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: 362.43

Molecular Weight (Monoisotopic): 362.1630

AlogP: 3.93

#Rotatable Bonds: 5

Polar Surface Area: 55.45

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.24

CX LogP: 4.09

CX LogD: 4.06

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.51

Np Likeness Score: -1.03

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