(2-bromo-3,5-dimethoxy-6-(3-methylbut-2-enyl)phenyl)(3,5-dichloro-2,6-dimethoxy-4-methylphenyl)methanone

ID: ALA2408956

PubChem CID: 73352154

Max Phase: Preclinical

Molecular Formula: C23H25BrCl2O5

Molecular Weight: 532.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(CC=C(C)C)c(C(=O)c2c(OC)c(Cl)c(C)c(Cl)c2OC)c1Br

Standard InChI:  InChI=1S/C23H25BrCl2O5/c1-11(2)8-9-13-14(28-4)10-15(29-5)18(24)16(13)21(27)17-22(30-6)19(25)12(3)20(26)23(17)31-7/h8,10H,9H2,1-7H3

Standard InChI Key:  BKKDVKYIAULMDY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   11.7859  -16.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7848  -17.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4928  -17.8117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2025  -17.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1997  -16.5796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4911  -16.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4886  -15.3571    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.9058  -16.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9109  -17.8097    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.0781  -16.1747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4926  -18.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0768  -17.8107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3694  -17.4016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0761  -18.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3680  -19.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3670  -19.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0749  -20.2608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7853  -19.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7833  -19.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4941  -20.2551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6588  -20.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6610  -18.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6626  -17.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9556  -17.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9571  -16.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2471  -17.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2003  -19.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0779  -15.3575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4964  -21.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6577  -21.0757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5715  -19.2411    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
  6  7  1  0
  5  8  1  0
  4  9  1  0
  1 10  1  0
  3 11  1  0
  2 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 16 21  1  0
 15 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 24 26  1  0
 11 27  1  0
 10 28  1  0
 20 29  1  0
 21 30  1  0
 19 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2408956

   [2-Bromo-3,5-dimethoxy-6-(3-methylbut-2-enyl)phenyl]-(3,5-dichloro-2,6-dimethoxy-4-methylphenyl)methanone

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: 532.26

Molecular Weight (Monoisotopic): 530.0262

AlogP: 6.84

#Rotatable Bonds: 8

Polar Surface Area: 53.99

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.02

CX LogD: 7.02

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.28

Np Likeness Score: 0.99

References

1. Augner D, Krut O, Slavov N, Gerbino DC, Sahl HG, Benting J, Nising CF, Hillebrand S, Krönke M, Schmalz HG..  (2013)  On the antibiotic and antifungal activity of pestalone, pestalachloride A, and structurally related compounds.,  76  (8): [PMID:23905700] [10.1021/np400301d]

Source

Source(1):

• Scientific Literature