(Z)-3-benzyl-5-(4-hydroxybenzylidene)furan-2(5H)-one

ID: ALA2228188

PubChem CID: 76333187

Max Phase: Preclinical

Molecular Formula: C18H14O3

Molecular Weight: 278.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O/C(=C\c2ccc(O)cc2)C=C1Cc1ccccc1

Standard InChI:  InChI=1S/C18H14O3/c19-16-8-6-14(7-9-16)11-17-12-15(18(20)21-17)10-13-4-2-1-3-5-13/h1-9,11-12,19H,10H2/b17-11-

Standard InChI Key:  YKBLFNMHMKABHJ-BOPFTXTBSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   21.5814  -24.4020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9191  -24.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2594  -24.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5150  -23.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3299  -23.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9180  -25.6986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0409  -23.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7480  -23.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4553  -23.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1624  -23.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1585  -24.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4517  -24.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7446  -24.4456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5540  -24.8090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8454  -24.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1400  -24.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4293  -24.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4241  -23.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1296  -23.1824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8402  -23.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8650  -24.8624    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA2228188

   (5Z)-3-benzyl-5-[(4-hydroxyphenyl)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: 278.31

Molecular Weight (Monoisotopic): 278.0943

AlogP: 3.46

#Rotatable Bonds: 3

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.29

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.02

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: 0.98

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