(5Z)-3-Benzyl-5-(cyanobenzylidene)furan-2(5H)-one

ID: ALA2228183

PubChem CID: 24861992

Max Phase: Preclinical

Molecular Formula: C19H13NO2

Molecular Weight: 287.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cccc(/C=C2/C=C(Cc3ccccc3)C(=O)O2)c1

Standard InChI:  InChI=1S/C19H13NO2/c20-13-16-8-4-7-15(9-16)11-18-12-17(19(21)22-18)10-14-5-2-1-3-6-14/h1-9,11-12H,10H2/b18-11-

Standard InChI Key:  LCONRNQYWHVINT-WQRHYEAKSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   18.8202  -20.8402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1580  -21.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4983  -20.8347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7539  -20.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5688  -20.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1569  -22.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2798  -19.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9869  -20.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6942  -19.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4013  -20.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3974  -20.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6906  -21.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9835  -20.8838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7929  -21.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0843  -20.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3789  -21.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6682  -20.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6630  -20.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3685  -19.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0791  -20.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1077  -19.6630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8173  -19.2577    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  1  5  1  0
  2  6  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
  8 13  2  0
  5  7  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
  3 14  1  0
 21 22  3  0
 10 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228183

   3-[(Z)-(4-benzyl-5-oxofuran-2-ylidene)methyl]benzonitrile

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: 287.32

Molecular Weight (Monoisotopic): 287.0946

AlogP: 3.63

#Rotatable Bonds: 3

Polar Surface Area: 50.09

Molecular Species: ┄

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.19

CX LogD: 4.19

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: 0.11

References

1. Teixeira RR, Barbosa LC, Forlani G, Piló-Veloso D, Walkimar de Mesquita Carneiro J..  (2008)  Synthesis of photosynthesis-inhibiting nostoclide analogues.,  56  (7): [PMID:18338868] [10.1021/jf072964g]

2. Teixeira RR, Pinheiro PF, Barbosa LC, Carneiro JW, Forlani G..  (2010)  QSAR modeling of photosynthesis-inhibiting nostoclide derivatives.,  66  (2): [PMID:19798697] [10.1002/ps.1855]

Source

Source(1):

• Scientific Literature