(Z)-2-[(3,5-Dimethoxy-4-hydroxyphenyl)methylene]-4,6-dihydroxy-3(2H)-benzofuranone

ID: ALA2288404

PubChem CID: 6476406

Max Phase: Preclinical

Molecular Formula: C17H14O7

Molecular Weight: 330.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\Oc3cc(O)cc(O)c3C2=O)cc(OC)c1O

Standard InChI:  InChI=1S/C17H14O7/c1-22-12-3-8(4-13(23-2)16(12)20)5-14-17(21)15-10(19)6-9(18)7-11(15)24-14/h3-7,18-20H,1-2H3/b14-5-

Standard InChI Key:  LOVMOOUQHWMIHZ-RZNTYIFUSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   16.6853  -17.3886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7716  -16.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0179  -16.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4659  -16.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8784  -17.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6409  -16.8456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2284  -17.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6409  -18.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4659  -18.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8464  -15.4256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2284  -18.9891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2284  -16.1312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4860  -16.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2005  -16.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9150  -16.1556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6294  -16.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6294  -17.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9150  -17.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2005  -17.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3439  -17.8056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9150  -18.6306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6294  -19.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3439  -16.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0584  -16.5681    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
 17 20  1  0
 21 22  1  0
 18 21  1  0
 23 24  1  0
 16 23  1  0
 13 14  1  0
  2 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2288404

   (2Z)-4,6-dihydroxy-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-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: 330.29

Molecular Weight (Monoisotopic): 330.0740

AlogP: 2.44

#Rotatable Bonds: 3

Polar Surface Area: 105.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.66

CX Basic pKa: ┄

CX LogP: 2.63

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: 0.85

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