(5Z)-3-Benzyl-5-(4-cyanobenzylidene)furan-2(5H)-one

ID: ALA2228179

PubChem CID: 24861988

Max Phase: Preclinical

Molecular Formula: C19H13NO2

Molecular Weight: 287.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(/C=C2/C=C(Cc3ccccc3)C(=O)O2)cc1

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

Standard InChI Key:  HSUZTRWPQXVVPI-WQRHYEAKSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   28.7503  -16.6428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0881  -17.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4284  -16.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6840  -15.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4989  -15.8653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0870  -17.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2099  -15.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9170  -15.8717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6243  -15.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3314  -15.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3275  -16.6924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6207  -17.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9136  -16.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7230  -17.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0144  -16.6475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3090  -17.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5983  -16.6541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5931  -15.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2986  -15.4233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0092  -15.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0338  -17.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7403  -17.5087    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
 11 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228179

   4-[(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: 0.21

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