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

ID: ALA2228176

PubChem CID: 24861946

Max Phase: Preclinical

Molecular Formula: C20H18O2

Molecular Weight: 290.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(/C=C2/C=C(Cc3ccccc3)C(=O)O2)cc1

Standard InChI:  InChI=1S/C20H18O2/c1-2-15-8-10-17(11-9-15)13-19-14-18(20(21)22-19)12-16-6-4-3-5-7-16/h3-11,13-14H,2,12H2,1H3/b19-13-

Standard InChI Key:  OWMCHCDGUKUNFS-UYRXBGFRSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    5.1055  -16.2425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4432  -16.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7835  -16.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391  -15.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8540  -15.4649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4421  -17.5391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5650  -15.0587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2721  -15.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9794  -15.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6865  -15.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6826  -16.2921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9758  -16.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2687  -16.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781  -16.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3695  -16.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6641  -16.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9534  -16.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482  -15.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6537  -15.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3643  -15.4288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3891  -16.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3865  -17.5201    0.0000 C   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
 11 21  1  0
 21 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228176

   (5Z)-3-benzyl-5-[(4-ethylphenyl)methylidene]furan-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: 290.36

Molecular Weight (Monoisotopic): 290.1307

AlogP: 4.32

#Rotatable Bonds: 4

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.78

Np Likeness Score: 0.52

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