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

ID: ALA1089358

PubChem CID: 46884270

Max Phase: Preclinical

Molecular Formula: C20H22FNO4

Molecular Weight: 359.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2ccccc2F)c(O)c1CN1CCCC1

Standard InChI:  InChI=1S/C20H22FNO4/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:  TUUBZJCYBDWIRY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   17.0361   -3.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0349   -4.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7497   -4.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4662   -4.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4633   -3.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7479   -2.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3201   -4.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6060   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7455   -2.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4587   -1.6934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813   -4.5841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1762   -2.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8922   -3.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1731   -2.1020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8920   -4.1594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6072   -4.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3211   -4.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3153   -3.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5995   -2.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5922   -2.0937    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.7495   -5.4110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0350   -5.8234    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2819   -5.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7297   -6.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1421   -6.8185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9490   -6.6470    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:

   

   ALA1089358

   (2-Fluorophenyl)-[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: 359.40

Molecular Weight (Monoisotopic): 359.1533

AlogP: 3.38

#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: 5.96

CX Basic pKa: 7.93

CX LogP: 2.76

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: -0.45

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