4-bromo-5-(bromomethylene)-3-dodecylfuran-2(5H)-one

ID: ALA1254014

PubChem CID: 10180544

Max Phase: Preclinical

Molecular Formula: C17H26Br2O2

Molecular Weight: 422.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCC1=C(Br)/C(=C/Br)OC1=O

Standard InChI:  InChI=1S/C17H26Br2O2/c1-2-3-4-5-6-7-8-9-10-11-12-14-16(19)15(13-18)21-17(14)20/h13H,2-12H2,1H3/b15-13-

Standard InChI Key:  NNNYZZORXYLITQ-SQFISAMPSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   10.8088    1.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4730    0.7329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1449    1.2118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8948    2.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0707    2.0034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0222    0.9738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9274    0.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0923    0.1422    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   12.3833    2.6656    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.5900    2.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7690    2.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2883    3.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4673    3.1823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9866    3.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1677    3.7717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6869    4.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659    4.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3850    5.0355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5640    4.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832    5.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622    5.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
 10 11  1  0
  1  2  1  0
 11 12  1  0
  1  6  2  0
 12 13  1  0
 13 14  1  0
  3  7  2  0
 14 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  1  0
  4  9  1  0
 18 19  1  0
  4  5  2  0
 19 20  1  0
  5 10  1  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1254014

   (5Z)-4-bromo-5-(bromomethylidene)-3-dodecylfuran-2-one

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: 422.20

Molecular Weight (Monoisotopic): 420.0300

AlogP: 6.74

#Rotatable Bonds: 11

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.93

CX LogD: 6.93

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.27

Np Likeness Score: 1.38

References

1. Steenackers HP, Levin J, Janssens JC, De Weerdt A, Balzarini J, Vanderleyden J, De Vos DE, De Keersmaecker SC..  (2010)  Structure-activity relationship of brominated 3-alkyl-5-methylene-2(5H)-furanones and alkylmaleic anhydrides as inhibitors of Salmonella biofilm formation and quorum sensing regulated bioluminescence in Vibrio harveyi.,  18  (14): [PMID:20580562] [10.1016/j.bmc.2010.05.055]

Source

Source(1):

• Scientific Literature