5-hydroxybenzo[b]furan-2-yl-(5-hydroxy-1Hindol-2-yl)methanone

ID: ALA226184

PubChem CID: 44423636

Max Phase: Preclinical

Molecular Formula: C17H11NO4

Molecular Weight: 293.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1cc2cc(O)ccc2[nH]1)c1cc2cc(O)ccc2o1

Standard InChI:  InChI=1S/C17H11NO4/c19-11-1-3-13-9(5-11)7-14(18-13)17(21)16-8-10-6-12(20)2-4-15(10)22-16/h1-8,18-20H

Standard InChI Key:  ZKIUEEGLQKCTHN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   10.3338  -19.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3303  -20.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0439  -21.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0468  -19.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7610  -19.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7589  -20.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5443  -20.8887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0318  -20.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5477  -19.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568  -20.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2675  -20.9389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2711  -19.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0901  -19.4277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9358  -18.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5502  -18.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2621  -18.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9766  -18.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9803  -17.3904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2636  -16.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5521  -17.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2640  -16.1509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6204  -19.3900    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:

   

   ALA226184

   5-hydroxybenzo[b]furan-2-yl-(5-hydroxy-1Hindol-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: 293.28

Molecular Weight (Monoisotopic): 293.0688

AlogP: 3.56

#Rotatable Bonds: 2

Polar Surface Area: 86.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: ┄

CX LogP: 2.92

CX LogD: 2.92

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.49

Np Likeness Score: -0.15

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