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

ID: ALA2228189

PubChem CID: 76329529

Max Phase: Preclinical

Molecular Formula: C19H16O4

Molecular Weight: 308.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2/C=C(Cc3ccccc3)C(=O)O2)cc1O

Standard InChI:  InChI=1S/C19H16O4/c1-22-18-8-7-14(11-17(18)20)10-16-12-15(19(21)23-16)9-13-5-3-2-4-6-13/h2-8,10-12,20H,9H2,1H3/b16-10-

Standard InChI Key:  RQSMQPUZDJMZRL-YBEGLDIGSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   30.7521  -24.4846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0898  -24.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4301  -24.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6857  -23.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5006  -23.7070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0887  -25.7812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2116  -23.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9187  -23.7134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6260  -23.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3331  -23.7153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3292  -24.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6224  -24.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9153  -24.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7247  -24.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0161  -24.4892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3107  -24.9017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6000  -24.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5948  -23.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3003  -23.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0109  -23.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0357  -24.9450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0427  -23.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.0331  -25.7621    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
 10 22  1  0
 21 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228189

   (5Z)-3-benzyl-5-[(3-hydroxy-4-methoxyphenyl)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: 308.33

Molecular Weight (Monoisotopic): 308.1049

AlogP: 3.47

#Rotatable Bonds: 4

Polar Surface Area: 55.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.77

CX Basic pKa: ┄

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.88

Np Likeness Score: 1.00

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