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

ID: ALA2228186

PubChem CID: 76311457

Max Phase: Preclinical

Molecular Formula: C18H14O3

Molecular Weight: 278.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O/C(=C\c2ccccc2O)C=C1Cc1ccccc1

Standard InChI:  InChI=1S/C18H14O3/c19-17-9-5-4-8-14(17)11-16-12-15(18(20)21-16)10-13-6-2-1-3-7-13/h1-9,11-12,19H,10H2/b16-11-

Standard InChI Key:  ACCNNWSXIFRIJA-WJDWOHSUSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    4.5648  -24.3649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9026  -24.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2429  -24.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4985  -23.5857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3134  -23.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9015  -25.6615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0243  -23.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7314  -23.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4387  -23.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1458  -23.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1420  -24.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4351  -24.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7280  -24.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374  -24.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8289  -24.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1234  -24.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4128  -24.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4076  -23.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130  -23.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8237  -23.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4396  -22.3658    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
  9 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228186

   (5Z)-3-benzyl-5-[(2-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: 9.09

CX Basic pKa: ┄

CX LogP: 4.03

CX LogD: 4.02

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: 0.82

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