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

ID: ALA1093733

PubChem CID: 46884330

Max Phase: Preclinical

Molecular Formula: C20H22ClNO4

Molecular Weight: 375.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2cccc(Cl)c2)c(O)c1CN1CCCC1

Standard InChI:  InChI=1S/C20H22ClNO4/c1-25-16-11-17(26-2)18(19(23)13-6-5-7-14(21)10-13)20(24)15(16)12-22-8-3-4-9-22/h5-7,10-11,24H,3-4,8-9,12H2,1-2H3

Standard InChI Key:  ODEJEKFSNWXRJZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   18.0986   -9.7166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0974  -10.5440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8122  -10.9569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5287  -10.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5258   -9.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8104   -9.3039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3826  -10.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6685  -10.5429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8080   -8.4789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5212   -8.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2438  -10.9549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2387   -9.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9547   -9.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2356   -8.4728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9545  -10.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6697  -10.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3836  -10.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3778   -9.6955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6620   -9.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8120  -11.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0975  -12.1942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3444  -11.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7922  -12.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2046  -13.1893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0115  -13.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0892   -9.2778    0.0000 Cl  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
  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
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 21  1  0
  6  1  1  0
 18 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093733

   (3-Chlorophenyl)-[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: 375.85

Molecular Weight (Monoisotopic): 375.1237

AlogP: 3.89

#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: 6.00

CX Basic pKa: 7.97

CX LogP: 3.22

CX LogD: 3.19

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: -0.34

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