(Z)-5-(3-bromo-4-hydroxybenzylidene)-4-(3,5-dibromo-4-methoxyphenyl)-3-(furan-2-carbonyl)furan-2(5H)-one

ID: ALA3585733

PubChem CID: 122179830

Max Phase: Preclinical

Molecular Formula: C23H13Br3O6

Molecular Weight: 625.06

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(Br)cc(C2=C(C(=O)c3ccco3)C(=O)O/C2=C\c2ccc(O)c(Br)c2)cc1Br

Standard InChI:  InChI=1S/C23H13Br3O6/c1-30-22-14(25)9-12(10-15(22)26)19-18(8-11-4-5-16(27)13(24)7-11)32-23(29)20(19)21(28)17-3-2-6-31-17/h2-10,27H,1H3/b18-8-

Standard InChI Key:  ZQTCTPAAEFHHAE-LSCVHKIXSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2010   -3.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2506    0.5865    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
    1.6137   -3.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1277    1.5822    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
    1.0972   -7.9127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1467   -1.8743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866    3.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9143   -5.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3890    0.9663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211   -8.3844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7938   -6.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6799    1.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9105    3.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9175    2.5336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6416   -7.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 Br  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
   -2.5973    1.5031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2008   -8.7105    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.3382   -5.9182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7638   -9.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956    2.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  3  1  0
  5  2  1  0
  6  1  1  0
  7  3  1  0
  8 12  1  0
  9  4  2  0
 10  6  1  0
 11 13  1  0
 12 14  2  0
 13  7  2  0
 14  7  1  0
 15 21  1  0
 16  2  2  0
 17 10  1  0
 18  9  1  0
 19  6  2  0
 20 25  1  0
 21 18  2  0
 22 10  2  0
 23 17  1  0
 24 22  1  0
 25 30  2  0
 26 12  1  0
 27 11  1  0
 28  8  1  0
 29 15  1  0
 30 18  1  0
 31 20  1  0
  5  4  1  0
 23 24  2  0
  8 11  2  0
 15 20  2  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3585733

   ---

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: 625.06

Molecular Weight (Monoisotopic): 621.8262

AlogP: 6.52

#Rotatable Bonds: 5

Polar Surface Area: 85.97

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.51

CX Basic pKa: ┄

CX LogP: 6.12

CX LogD: 5.88

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.20

Np Likeness Score: 0.51

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