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

ID: ALA226182

PubChem CID: 13471348

Max Phase: Preclinical

Molecular Formula: C21H14O7

Molecular Weight: 378.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Oc1ccc2oc(C(=O)c3cc4cc(OC(C)=O)ccc4o3)cc2c1

Standard InChI:  InChI=1S/C21H14O7/c1-11(22)25-15-3-5-17-13(7-15)9-19(27-17)21(24)20-10-14-8-16(26-12(2)23)4-6-18(14)28-20/h3-10H,1-2H3

Standard InChI Key:  UACDZFCKAGJOFV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   11.7963  -13.8002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7928  -14.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5064  -15.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5093  -13.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2235  -13.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2214  -14.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0068  -14.8845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4943  -14.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0102  -13.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3193  -14.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7300  -14.9347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7336  -13.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5526  -13.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3983  -12.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0127  -12.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7246  -12.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4391  -12.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4428  -11.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7261  -10.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0146  -11.3824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7265  -10.1467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4412   -9.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4416   -8.9096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1555  -10.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0829  -13.3858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3674  -13.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6540  -13.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3652  -14.6214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 21 22  1  0
  5  6  1  0
 22 23  2  0
 10 11  2  0
 22 24  1  0
  1 25  1  0
 10 12  1  0
 25 26  1  0
 12 13  1  0
 26 27  1  0
  2  3  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA226182

   Bis(5-acetoxybenzo[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: 378.34

Molecular Weight (Monoisotopic): 378.0740

AlogP: 4.26

#Rotatable Bonds: 4

Polar Surface Area: 95.95

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.81

CX LogD: 2.81

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.30

Np Likeness Score: -0.06

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