(Z)-2-[(3,4-Dimethoxyphenyl)methylene]-4,6-dihydroxy-3(2H)-benzofuranone

ID: ALA2288403

PubChem CID: 59971483

Max Phase: Preclinical

Molecular Formula: C17H14O6

Molecular Weight: 314.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C2\Oc3cc(O)cc(O)c3C2=O)cc1OC

Standard InChI:  InChI=1S/C17H14O6/c1-21-12-4-3-9(5-13(12)22-2)6-15-17(20)16-11(19)7-10(18)8-14(16)23-15/h3-8,18-19H,1-2H3/b15-6-

Standard InChI Key:  BZIWUSANDYRNLN-UUASQNMZSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   19.2375  -15.8613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1512  -16.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9049  -17.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4569  -16.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0444  -15.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2819  -16.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6944  -15.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2819  -14.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4569  -14.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0764  -17.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6944  -14.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6944  -17.1188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4368  -17.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7223  -16.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0078  -17.0943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2933  -16.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2933  -15.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0078  -15.4443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7223  -15.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5789  -15.4443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8644  -15.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5789  -17.0943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8644  -16.6818    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  1  0
  4  5  1  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  5  9  2  0
  4  6  2  0
  3 10  2  0
  8 11  1  0
  6 12  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 20 21  1  0
 17 20  1  0
 22 23  1  0
 16 22  1  0
 13 14  1  0
  2 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288403

   (2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-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: 314.29

Molecular Weight (Monoisotopic): 314.0790

AlogP: 2.73

#Rotatable Bonds: 3

Polar Surface Area: 85.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.70

CX Basic pKa: ┄

CX LogP: 2.93

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.85

Np Likeness Score: 0.67

References

1. Zhang M, Xu XH, Cui Y, Xie LG, Kong CH..  (2012)  Synthesis and herbicidal potential of substituted aurones.,  68  (11): [PMID:22718431] [10.1002/ps.3339]

Source

Source(1):

• Scientific Literature