(2-bromophenyl)(2-hydroxy-4,6-dimethoxy-3-(morpholinomethyl)phenyl)methanone

ID: ALA1088969

PubChem CID: 46884332

Max Phase: Preclinical

Molecular Formula: C20H22BrNO5

Molecular Weight: 436.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2ccccc2Br)c(O)c1CN1CCOCC1

Standard InChI:  InChI=1S/C20H22BrNO5/c1-25-16-11-17(26-2)18(19(23)13-5-3-4-6-15(13)21)20(24)14(16)12-22-7-9-27-10-8-22/h3-6,11,24H,7-10,12H2,1-2H3

Standard InChI Key:  LZBAFBMRJORJPE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    2.7694  -16.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7682  -17.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831  -17.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995  -17.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1966  -16.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813  -15.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0534  -17.5434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393  -17.1304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788  -15.0664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1920  -14.6517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9146  -17.5424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096  -15.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6256  -16.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9064  -15.0603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6253  -17.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3405  -17.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0544  -17.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0486  -16.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3329  -15.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3255  -15.0520    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.4829  -18.3694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683  -18.7817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0551  -18.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3426  -18.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3382  -19.6048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0524  -20.0197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7710  -19.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 12 13  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1088969

   (2-Bromophenyl)-[2-hydroxy-4,6-dimethoxy-3-(morpholin-4-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: 436.30

Molecular Weight (Monoisotopic): 435.0681

AlogP: 3.24

#Rotatable Bonds: 6

Polar Surface Area: 68.23

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.44

CX Basic pKa: 5.23

CX LogP: 3.69

CX LogD: 2.91

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.38

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