3,4,5-Tribromo-2-(3,5-dibromo-2-hydroxy-phenoxy)-phenol

ID: ALA149159

Cas Number: 170473-61-7

PubChem CID: 11801671

Max Phase: Preclinical

Molecular Formula: C12H5Br5O3

Molecular Weight: 596.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1cc(Br)c(Br)c(Br)c1Oc1cc(Br)cc(Br)c1O

Standard InChI:  InChI=1S/C12H5Br5O3/c13-4-1-6(15)11(19)8(2-4)20-12-7(18)3-5(14)9(16)10(12)17/h1-3,18-19H

Standard InChI Key:  WMMMSBGZKIDZDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
   12.9569   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9557   -6.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6706   -6.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3870   -6.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3841   -5.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6688   -4.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0971   -4.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8131   -5.2409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8128   -6.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5280   -6.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2419   -6.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2361   -5.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5204   -4.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2409   -6.4893    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   16.5130   -3.9979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5307   -7.2983    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.9476   -4.8111    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.1021   -6.4882    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   13.6663   -4.0122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6704   -7.3152    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
  2  3  1  0
 10 11  2  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
 13  8  1  0
  1  2  2  0
  2 14  1  0
  5  7  1  0
 13 15  1  0
  3  4  2  0
 10 16  1  0
  7  8  1  0
 12 17  1  0
  4 18  1  0
  8  9  2  0
  6 19  1  0
  4  5  1  0
  3 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA149159

   Phenol, 3,4,5-tribromo-2-(3,5-dibromo-2-hydroxyphenoxy)-

Molecule Features

Natural Product: Yes

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: 596.69

Molecular Weight (Monoisotopic): 591.6156

AlogP: 6.70

#Rotatable Bonds: 2

Polar Surface Area: 49.69

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.85

CX Basic pKa: ┄

CX LogP: 6.71

CX LogD: 4.00

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.38

Np Likeness Score: 0.98

References

1. de la Fuente JA, Manzanaro S, Martín MJ, de Quesada TG, Reymundo I, Luengo SM, Gago F..  (2003)  Synthesis, activity, and molecular modeling studies of novel human aldose reductase inhibitors based on a marine natural product.,  46  (24): [PMID:14613323] [10.1021/jm030957n]

2. Hanif N, Tanaka J, Setiawan A, Trianto A, de Voogd NJ, Murni A, Tanaka C, Higa T..  (2007)  Polybrominated diphenyl ethers from the Indonesian sponge Lamellodysidea herbacea.,  70  (3): [PMID:17311456] [10.1021/np0605081]

3. Fu X, Schmitz FJ, Govindan M, Abbas SA, Hanson KM, Horton PA, Crews P, Laney M, Schatzman RC..  (1995)  Enzyme inhibitors: new and known polybrominated phenols and diphenyl ethers from four Indo-Pacific Dysidea sponges.,  58  (9): [PMID:7494145] [10.1021/np50123a008]

4. Calcul L, Chow R, Oliver AG, Tenney K, White KN, Wood AW, Fiorilla C, Crews P..  (2009)  NMR strategy for unraveling structures of bioactive sponge-derived oxy-polyhalogenated diphenyl ethers.,  72  (3): [PMID:19323567] [10.1021/np800737z]

5. Liu H, Lohith K, Rosario M, Pulliam TH, O'Connor RD, Bell LJ, Bewley CA..  (2016)  Polybrominated Diphenyl Ethers: Structure Determination and Trends in Antibacterial Activity.,  79  (7): [PMID:27399938] [10.1021/acs.jnatprod.6b00229]

Source

Source(1):

• Scientific Literature