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

ID: ALA2259971

PubChem CID: 49774066

Max Phase: Preclinical

Molecular Formula: C14H18Br3NO3

Molecular Weight: 488.01

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H18Br3NO3/c1-14(2)5-7-9(15)10(16)11(17)13(12(7)21-14)20-6-8(19)18(3)4/h8,19H,5-6H2,1-4H3

Standard InChI Key:  HHWKWPCRNYWAFB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   15.8611  -16.9160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2875  -16.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1487  -15.6762    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.0044  -20.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2885  -18.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5750  -18.1539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8622  -16.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5748  -17.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5668  -16.5001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2872  -16.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2887  -19.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0773  -15.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5729  -15.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7173  -19.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1512  -17.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5705  -14.8507    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   19.1512  -15.9076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0777  -17.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5755  -19.8040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0064  -19.8036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.1473  -17.3279    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
 13 16  1  0
  5 11  1  0
 13  7  1  0
 12 10  1  0
 10 13  2  0
 20 14  1  0
  7  1  2  0
  1  8  1  0
  9 12  1  0
 20  4  1  0
  1 21  1  0
  8  6  1  0
 10  2  1  0
 11 19  1  0
 11 20  1  0
  9 17  1  0
  9 15  1  0
  2 18  1  0
 18  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2259971

   1-(dimethylamino)-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: 488.01

Molecular Weight (Monoisotopic): 484.8837

AlogP: 3.95

#Rotatable Bonds: 4

Polar Surface Area: 41.93

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.80

CX Basic pKa: 7.22

CX LogP: 4.36

CX LogD: 4.14

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.52

Np Likeness Score: 0.45

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