(2-bromophenyl)(2-hydroxy-4,6-dimethoxy-3-(pyrrolidin-1-ylmethyl)phenyl)methanone

ID: ALA1091049

PubChem CID: 46884375

Max Phase: Preclinical

Molecular Formula: C20H22BrNO4

Molecular Weight: 420.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2ccccc2Br)c(O)c1CN1CCCC1

Standard InChI:  InChI=1S/C20H22BrNO4/c1-25-16-11-17(26-2)18(19(23)13-7-3-4-8-15(13)21)20(24)14(16)12-22-9-5-6-10-22/h3-4,7-8,11,24H,5-6,9-10,12H2,1-2H3

Standard InChI Key:  OABYAGIMRITJGD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   18.1819  -15.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1807  -16.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8956  -17.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6120  -16.7477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6091  -15.9172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8938  -15.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4659  -17.1601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7518  -16.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8913  -14.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6045  -14.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3271  -17.1591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3221  -15.5020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0381  -15.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3189  -14.6770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0378  -16.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7530  -17.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4669  -16.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4611  -15.8997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7454  -15.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7380  -14.6687    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   18.8954  -17.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1808  -18.3984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.4277  -18.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8755  -18.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2879  -19.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0949  -19.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  1  2  2  0
 12 14  2  0
  2  7  1  0
 13 15  2  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
 17 18  1  0
  6  9  1  0
 18 19  2  0
 19 13  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
  3 21  1  0
  2  3  1  0
 21 22  1  0
 22 23  1  0
  4 11  1  0
  5  6  2  0
  5 12  1  0
  6  1  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091049

   (2-Bromophenyl)-[2-hydroxy-4,6-dimethoxy-3-(pyrrolidin-1-ylmethyl)phenyl]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: 420.30

Molecular Weight (Monoisotopic): 419.0732

AlogP: 4.00

#Rotatable Bonds: 6

Polar Surface Area: 59.00

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.99

CX Basic pKa: 7.96

CX LogP: 3.39

CX LogD: 3.36

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.72

Np Likeness Score: -0.20

References

1. Bandgar BP, Patil SA, Totre JV, Korbad BL, Gacche RN, Hote BS, Jalde SS, Chavan HV..  (2010)  Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity.,  20  (7): [PMID:20207143] [10.1016/j.bmcl.2010.02.001]

Source

Source(1):

• Scientific Literature