hemi-chrysophaentin

ID: ALA2418096

PubChem CID: 60164930

Max Phase: Preclinical

Molecular Formula: C18H18Cl2O4

Molecular Weight: 369.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C/C=C(/Cl)Cc2cc(O)cc(O)c2)c(OC)cc1Cl

Standard InChI:  InChI=1S/C18H18Cl2O4/c1-23-17-10-16(20)18(24-2)8-12(17)3-4-13(19)5-11-6-14(21)9-15(22)7-11/h4,6-10,21-22H,3,5H2,1-2H3/b13-4+

Standard InChI Key:  MKTUZAYNCRKLDS-YIXHJXPBSA-N

Molfile:  

     RDKit          2D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.6387   -0.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 O   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
    0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3476    5.8478    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0092    6.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0123    7.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2836    8.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2775    9.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3143   10.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0246   10.5050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    9.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3622   10.3455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3144    8.2497    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
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    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
    0.0000   -2.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  5 19  2  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  2  0
 23  3  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2418096

   (E)-5-(2-chloro-4-(4-chloro-2,5-dimethoxyphenyl)but-2-enyl)benzene-1,3-diol

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: 369.24

Molecular Weight (Monoisotopic): 368.0582

AlogP: 4.68

#Rotatable Bonds: 6

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.18

CX Basic pKa: ┄

CX LogP: 4.80

CX LogD: 4.79

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.78

Np Likeness Score: 0.38

References

1. Keffer JL, Huecas S, Hammill JT, Wipf P, Andreu JM, Bewley CA..  (2013)  Chrysophaentins are competitive inhibitors of FtsZ and inhibit Z-ring formation in live bacteria.,  21  (18): [PMID:23932448] [10.1016/j.bmc.2013.07.033]

2. Li X, Ma S..  (2015)  Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.,  95  [PMID:25791674] [10.1016/j.ejmech.2015.03.026]

3. Haranahalli K, Tong S, Ojima I..  (2016)  Recent advances in the discovery and development of antibacterial agents targeting the cell-division protein FtsZ.,  24  (24): [PMID:27189886] [10.1016/j.bmc.2016.05.003]

4.  (2015)  Chrysophaentin analogs that inhibit FtsZ protein, 

Source

Source(2):

• Scientific Literature
• BindingDB Database