bis(5-hydroxybenzo[b]furan-2-yl)methanone

ID: ALA225826

PubChem CID: 13454380

Max Phase: Preclinical

Molecular Formula: C17H10O5

Molecular Weight: 294.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1cc2cc(O)ccc2o1)c1cc2cc(O)ccc2o1

Standard InChI:  InChI=1S/C17H10O5/c18-11-1-3-13-9(5-11)7-15(21-13)17(20)16-8-10-6-12(19)2-4-14(10)22-16/h1-8,18-19H

Standard InChI Key:  TYHFGEDRLCAJMH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   11.2880   -6.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2844   -7.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9981   -7.8175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0010   -6.1645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7152   -6.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7131   -7.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4985   -7.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9860   -6.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5019   -6.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8110   -6.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2217   -7.7097    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2253   -6.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0443   -6.1986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8900   -5.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5043   -4.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2163   -5.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9307   -4.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9345   -4.1613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2178   -3.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5063   -4.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2182   -2.9217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5746   -6.1608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
  2  3  1  0
  3  6  2  0
 13 16  1  0
 15 14  1  0
 14 12  2  0
  1  2  2  0
  5  4  2  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
  8  9  2  0
 18 19  1  0
  9  5  1  0
 19 20  2  0
 20 15  1  0
  4  1  1  0
 19 21  1  0
  8 10  1  0
  1 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA225826

   Bis(5-hydroxybenzo[b]furan-2-yl)methanone

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: 294.26

Molecular Weight (Monoisotopic): 294.0528

AlogP: 3.82

#Rotatable Bonds: 2

Polar Surface Area: 83.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.98

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: 0.13

References

1. Mahboobi S, Uecker A, Cénac C, Sellmer A, Eichhorn E, Elz S, Böhmer FD, Dove S..  (2007)  Inhibition of FLT3 and PDGFR tyrosine kinase activity by bis(benzo[b]furan-2-yl)methanones.,  15  (5): [PMID:17210255] [10.1016/j.bmc.2006.12.011]

Source

Source(1):

• Scientific Literature