(Z)-3-(3-Bromo-4-hydroxybenzoyl)-5-(3-bromo-4-hydroxybenzylidene)-4-(3,5-dibromo-4-hydroxyphenyl)-furan-2(5H)-one

ID: ALA3585711

PubChem CID: 122179809

Max Phase: Preclinical

Molecular Formula: C24H12Br4O6

Molecular Weight: 715.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1O/C(=C\c2ccc(O)c(Br)c2)C(c2cc(Br)c(O)c(Br)c2)=C1C(=O)c1ccc(O)c(Br)c1

Standard InChI:  InChI=1S/C24H12Br4O6/c25-13-5-10(1-3-17(13)29)6-19-20(12-8-15(27)23(32)16(28)9-12)21(24(33)34-19)22(31)11-2-4-18(30)14(26)7-11/h1-9,29-30,32H/b19-6-

Standard InChI Key:  HUQPYUYTQWIVIT-SWNXQHNESA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5972    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951    3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786    3.8595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3371    5.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056    3.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2318    3.4007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4202    4.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8040    3.7286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9947    2.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8016    1.3317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4177    1.9104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2161    6.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4096    6.3821    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1284    6.2561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1018    1.7778    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6046    7.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4828    9.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8689   10.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3767   10.6142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4984    9.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1123    8.0296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8855   11.7091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.7000    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    6.9542    0.1414    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.3046    9.5203    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.7585    4.4559    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 12 13  1  0
 19 20  2  0
 11 19  1  0
 10 21  2  0
 16 22  1  0
  5 23  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 19 24  1  0
 27 30  1  0
  6 31  1  0
 17 32  1  0
 28 33  1  0
 15 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3585711

   ---

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: 715.97

Molecular Weight (Monoisotopic): 711.7367

AlogP: 7.09

#Rotatable Bonds: 4

Polar Surface Area: 104.06

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 5.79

CX Basic pKa: ┄

CX LogP: 7.38

CX LogD: 4.71

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.15

Np Likeness Score: 0.69

References

1. Boulangé A, Parraga J, Galán A, Cabedo N, Leleu S, Sanz MJ, Cortes D, Franck X..  (2015)  Synthesis and antibacterial activities of cadiolides A, B and C and analogues.,  23  (13): [PMID:25913865] [10.1016/j.bmc.2015.04.010]

Source

Source(1):

• Scientific Literature