2,3,4,5-Tetrabromo-6-(3,5-dibromo-2-hydroxy-phenoxy)-phenol

ID: ALA150098

Cas Number: 80246-27-1

PubChem CID: 339231

Max Phase: Preclinical

Molecular Formula: C12H4Br6O3

Molecular Weight: 675.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1c(Br)cc(Br)cc1Oc1c(O)c(Br)c(Br)c(Br)c1Br

Standard InChI:  InChI=1S/C12H4Br6O3/c13-3-1-4(14)10(19)5(2-3)21-12-9(18)7(16)6(15)8(17)11(12)20/h1-2,19-20H

Standard InChI Key:  OMYZFHYKAPRFFQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -3.0848  -16.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0859  -17.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3711  -18.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6547  -17.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6575  -16.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3729  -16.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9446  -16.3728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2286  -16.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2288  -17.6053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4863  -18.0150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2002  -17.5997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1945  -16.7705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4787  -16.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8007  -18.0309    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4713  -15.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395  -18.0299    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3754  -15.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3713  -18.8569    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7993  -16.3793    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.4890  -18.8400    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9059  -16.3528    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  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
  4 16  1  0
  7  8  1  0
  6 17  1  0
  3 18  1  0
  8  9  2  0
  1 19  1  0
  4  5  1  0
 10 20  1  0
  9 10  1  0
 12 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA150098

   2,3,4,5-Tetrabromo-6-(3,5-dibromo-2-hydroxyphenoxy)phenol

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: 675.58

Molecular Weight (Monoisotopic): 669.5261

AlogP: 7.47

#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: 4.74

CX Basic pKa: ┄

CX LogP: 7.48

CX LogD: 3.80

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.26

Np Likeness Score: 0.85

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. Segraves EN, Shah RR, Segraves NL, Johnson TA, Whitman S, Sui JK, Kenyon VA, Cichewicz RH, Crews P, Holman TR..  (2004)  Probing the activity differences of simple and complex brominated aryl compounds against 15-soybean, 15-human, and 12-human lipoxygenase.,  47  (16): [PMID:15267244] [10.1021/jm049872s]

3. 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]

4. Liu H, Namikoshi M, Meguro S, Nagai H, Kobayashi H, Yao X..  (2004)  Isolation and characterization of polybrominated diphenyl ethers as inhibitors of microtubule assembly from the marine sponge Phyllospongia dendyi collected at Palau.,  67  (3): [PMID:15043436] [10.1021/np0304621]

5. 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]

6. 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]

7. 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