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

ID: ALA1093731

PubChem CID: 46884328

Max Phase: Preclinical

Molecular Formula: C20H22ClNO5

Molecular Weight: 391.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2cccc(Cl)c2)c(O)c1CN1CCOCC1

Standard InChI:  InChI=1S/C20H22ClNO5/c1-25-16-11-17(26-2)18(19(23)13-4-3-5-14(21)10-13)20(24)15(16)12-22-6-8-27-9-7-22/h3-5,10-11,24H,6-9,12H2,1-2H3

Standard InChI Key:  KLFRQQKLDHGYOA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
    3.3069   -9.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3057  -10.4857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0206  -10.8985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7370  -10.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341   -9.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0188   -9.2455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5909  -10.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768  -10.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0163   -8.4205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295   -8.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4521  -10.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4471   -9.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1631   -9.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4439   -8.4145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1628  -10.4719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8780  -10.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5919  -10.4664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5861   -9.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8704   -9.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0204  -11.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3058  -12.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5926  -11.7248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801  -12.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8757  -12.9590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5899  -13.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3085  -12.9634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2976   -9.2194    0.0000 Cl  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
  3 20  1  0
  9 10  1  0
 20 21  1  0
 21 22  1  0
  2  3  1  0
  4 11  1  0
  5  6  2  0
  5 12  1  0
  6  1  1  0
 21 26  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 12 13  1  0
 18 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093731

   (3-Chlorophenyl)-[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: 391.85

Molecular Weight (Monoisotopic): 391.1187

AlogP: 3.13

#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: 6.46

CX Basic pKa: 5.25

CX LogP: 3.53

CX LogD: 2.76

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.76

Np Likeness Score: -0.51

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