4,5,6-Tribromo-7-O-[3-(diethylamino)-2-hydroxypropyl]-2,3-dihydro-2,2-dimethylbenzofuran

ID: ALA2259972

PubChem CID: 49774067

Max Phase: Preclinical

Molecular Formula: C16H22Br3NO3

Molecular Weight: 516.07

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(O)COc1c(Br)c(Br)c(Br)c2c1OC(C)(C)C2

Standard InChI:  InChI=1S/C16H22Br3NO3/c1-5-20(6-2)10(21)8-22-15-13(19)12(18)11(17)9-7-16(3,4)23-14(9)15/h10,21H,5-8H2,1-4H3

Standard InChI Key:  STHBPLHXEPPZCZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    9.0411  -19.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4684  -19.6703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3284  -18.4298    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   11.1857  -23.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4694  -21.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7554  -20.9088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0422  -18.8423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7552  -20.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7483  -19.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4681  -18.8387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4696  -22.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2585  -18.5789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8984  -23.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7534  -18.4293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6150  -22.5517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8989  -22.1428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3330  -19.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7510  -17.6038    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.3330  -18.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2589  -19.9254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7559  -22.5598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1877  -22.5594    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3269  -20.0825    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  8  2  2  0
  7  3  1  0
  6  5  1  0
 14 18  1  0
  5 11  1  0
 14  7  1  0
 12 10  1  0
 10 14  2  0
 22 16  1  0
  7  1  2  0
  1  8  1  0
  9 12  1  0
 16 15  1  0
 22  4  1  0
  1 23  1  0
  8  6  1  0
 10  2  1  0
 11 21  1  0
 11 22  1  0
  9 19  1  0
  9 17  1  0
  2 20  1  0
  4 13  1  0
 20  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2259972

   1-(diethylamino)-2-[(4,5,6-tribromo-2,2-dimethyl-3H-benzofuran-7-yl)oxy]ethanol

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: 516.07

Molecular Weight (Monoisotopic): 512.9150

AlogP: 4.73

#Rotatable Bonds: 6

Polar Surface Area: 41.93

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.79

CX Basic pKa: 7.77

CX LogP: 5.07

CX LogD: 4.54

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.44

Np Likeness Score: 0.19

References

1. Kossakowski J, Ostrowska K, Struga M, Stefanska J.  (2009)  Synthesis of new derivatives of 2,2-dimethyl-2,3-dihydro-7-benzo[b]furanol with potential antimicrobial activity,  18  (7): [10.1007/s00044-008-9149-5]

Source

Source(1):

• Scientific Literature