8-Bromo-3-methoxy-4-methyl-9-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulene

ID: ALA4583629

PubChem CID: 146373843

Max Phase: Preclinical

Molecular Formula: C22H25BrO4

Molecular Weight: 433.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1C)CCCC(Br)=C2c1cc(OC)c(OC)c(OC)c1

Standard InChI:  InChI=1S/C22H25BrO4/c1-13-15-7-6-8-17(23)21(16(15)9-10-18(13)24-2)14-11-19(25-3)22(27-5)20(12-14)26-4/h9-12H,6-8H2,1-5H3

Standard InChI Key:  RYKJGTUFWYSDIT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   40.2184  -25.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2173  -25.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9295  -26.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6432  -25.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6404  -25.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9277  -24.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9280  -27.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6645  -27.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.8483  -28.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3391  -29.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.5189  -29.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0057  -28.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1876  -27.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5860  -27.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8022  -27.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6235  -28.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.2265  -28.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9252  -23.9129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   41.6358  -23.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3507  -24.7282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.0641  -25.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5065  -24.7346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.5063  -23.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.0479  -29.4078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8396  -28.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.2338  -27.7438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.3074  -27.0503    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
  7  8  2  0
  8  9  1  0
  7 13  1  0
  9 10  1  0
 10 11  1  0
 12 11  1  0
  3  7  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  6 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  1  0
  1 22  1  0
 22 23  1  0
 17 24  1  0
 16 25  1  0
 25 26  1  0
  8 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4583629

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 433.34

Molecular Weight (Monoisotopic): 432.0936

AlogP: 5.52

#Rotatable Bonds: 5

Polar Surface Area: 36.92

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: 0.41

References

1. Niu H, Strecker TE, Gerberich JL, Campbell JW, Saha D, Mondal D, Hamel E, Chaplin DJ, Mason RP, Trawick ML, Pinney KG..  (2019)  Structure Guided Design, Synthesis, and Biological Evaluation of Novel Benzosuberene Analogues as Inhibitors of Tubulin Polymerization.,  62  (11): [PMID:31059248] [10.1021/acs.jmedchem.9b00551]

Source

Source(1):

• Scientific Literature