4,5,6-Tribromo-7-O-[2-hydroxy-3-(isopropylamino)propyl]-2,3-dihydro-2,2-dimethylbenzofuran

ID: ALA2259968

PubChem CID: 44551657

Max Phase: Preclinical

Molecular Formula: C15H20Br3NO3

Molecular Weight: 502.04

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H20Br3NO3/c1-7(2)19-9(20)6-21-14-12(18)11(17)10(16)8-5-15(3,4)22-13(8)14/h7,9,19-20H,5-6H2,1-4H3

Standard InChI Key:  QYCUPOPALGGQDP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   17.8150   -1.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8139   -2.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5287   -2.8110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5269   -1.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2422   -1.5671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2425   -2.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0330   -2.6548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5213   -1.9822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0326   -1.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5289   -3.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1039   -2.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1039   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0991   -2.8101    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.1005   -1.1585    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.5244   -0.3330    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   19.2435   -4.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2437   -4.8733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9583   -5.2856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5294   -5.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9585   -6.1106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6731   -6.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2441   -6.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
  8 11  1  0
  8 12  1  0
  2 13  1  0
  1 14  1  0
  4 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2259968

   1-(isopropylamino)-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: 502.04

Molecular Weight (Monoisotopic): 498.8993

AlogP: 4.38

#Rotatable Bonds: 5

Polar Surface Area: 50.72

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.09

CX Basic pKa: 8.59

CX LogP: 4.75

CX LogD: 3.53

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.46

Np Likeness Score: 0.51

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