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

ID: ALA1092123

PubChem CID: 46884423

Max Phase: Preclinical

Molecular Formula: C20H22FNO4

Molecular Weight: 359.40

Molecule Type: Small molecule

Names and Identifiers

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

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

Molfile:  

     RDKit          2D

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   17.4641  -24.4690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1789  -24.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8953  -24.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8925  -23.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1771  -23.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7493  -24.8809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0351  -24.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1746  -22.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8879  -21.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6105  -24.8799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6054  -23.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3214  -23.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6023  -22.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3212  -24.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0363  -24.8650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7502  -24.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7445  -23.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0287  -23.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1787  -25.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4641  -26.1192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7111  -25.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1589  -26.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5712  -27.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3782  -26.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4559  -23.2028    0.0000 F   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:

   

   ALA1092123

   (3-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: 6.00

CX Basic pKa: 7.97

CX LogP: 2.76

CX LogD: 2.73

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: -0.43

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