bis(6-hydroxybenzo[b]furan-2-yl)methanone

ID: ALA225827

PubChem CID: 13393486

Max Phase: Preclinical

Molecular Formula: C17H10O5

Molecular Weight: 294.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1cc2ccc(O)cc2o1)c1cc2ccc(O)cc2o1

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

Standard InChI Key:  RMZPEAFTFQMIEY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -3.7245  -12.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7281  -13.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0144  -13.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115  -11.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2973  -12.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994  -13.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5140  -13.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0265  -12.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5106  -11.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2015  -12.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2092  -13.3764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2128  -11.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0318  -11.8652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225  -11.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4918  -10.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038  -11.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182  -10.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9220   -9.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2053   -9.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4938   -9.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6376   -9.4173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4440  -13.4791    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
 18 21  1  0
  8 10  1  0
  2 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA225827

   Bis(6-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: 8.80

CX Basic pKa: ┄

CX LogP: 2.98

CX LogD: 2.97

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.55

Np Likeness Score: 0.21

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