2-((3-Methoxy-9-(3,4,5-trimethoxyphenyl)-6,7-dihydro-5H-benzo[7]annulen-4-yl)oxy)ethan-1-ol

ID: ALA4547567

PubChem CID: 146373868

Max Phase: Preclinical

Molecular Formula: C23H28O6

Molecular Weight: 400.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C2=CCCCc3c2ccc(OC)c3OCCO)cc(OC)c1OC

Standard InChI:  InChI=1S/C23H28O6/c1-25-19-10-9-17-16(7-5-6-8-18(17)22(19)29-12-11-24)15-13-20(26-2)23(28-4)21(14-15)27-3/h7,9-10,13-14,24H,5-6,8,11-12H2,1-4H3

Standard InChI Key:  ZJUOBVLONOOXJS-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   18.7114  -25.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7103  -25.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4225  -26.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1363  -25.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1334  -25.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4207  -24.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4210  -27.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1575  -27.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3413  -28.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8362  -28.9866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0160  -28.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4987  -28.3440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6806  -27.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0790  -26.9906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2952  -27.2318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1165  -28.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7195  -28.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4182  -23.8922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1288  -23.4774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8437  -24.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5571  -25.1135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9995  -24.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9993  -23.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5409  -29.3871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3326  -28.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7309  -27.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7569  -29.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1515  -29.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3674  -29.3218    0.0000 O   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
 24 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547567

   ---

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: 400.47

Molecular Weight (Monoisotopic): 400.1886

AlogP: 3.86

#Rotatable Bonds: 8

Polar Surface Area: 66.38

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.55

CX LogD: 3.55

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: 0.74

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