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

ID: ALA1091429

PubChem CID: 46884377

Max Phase: Preclinical

Molecular Formula: C21H24FNO4

Molecular Weight: 373.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2cccc(F)c2)c(O)c1CN1CCCCC1

Standard InChI:  InChI=1S/C21H24FNO4/c1-26-17-12-18(27-2)19(20(24)14-7-6-8-15(22)11-14)21(25)16(17)13-23-9-4-3-5-10-23/h6-8,11-12,25H,3-5,9-10,13H2,1-2H3

Standard InChI Key:  AYYZBQFQHSBUDN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.2361  -23.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2349  -24.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9497  -24.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6662  -24.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6633  -23.1713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9479  -22.7622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5201  -24.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8060  -24.0012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9455  -21.9372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6587  -21.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3813  -24.4132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3762  -22.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0922  -23.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3731  -21.9311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0920  -23.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8072  -24.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5211  -23.9831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5153  -23.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7995  -22.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9495  -25.2402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2350  -25.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5217  -25.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8093  -25.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8048  -26.4756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5190  -26.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2377  -26.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2267  -22.7361    0.0000 F   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:

   

   ALA1091429

   (3-Fluorophenyl)-[2-hydroxy-4,6-dimethoxy-3-(piperidin-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: 373.42

Molecular Weight (Monoisotopic): 373.1689

AlogP: 3.77

#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: 5.70

CX Basic pKa: 8.14

CX LogP: 3.19

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.42

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