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

ID: ALA1091435

PubChem CID: 46884376

Max Phase: Preclinical

Molecular Formula: C20H22FNO5

Molecular Weight: 375.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H22FNO5/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:  TXYUGGSDJITCKY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.0266  -23.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7414  -24.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4578  -23.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550  -22.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7396  -22.4539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118  -24.1059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5976  -23.6929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7371  -21.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4504  -21.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1730  -24.1049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1679  -22.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8839  -22.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1648  -21.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8837  -23.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5988  -24.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3127  -23.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3070  -22.8455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5912  -22.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7412  -24.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0266  -25.3442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3134  -24.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6010  -25.3419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5965  -26.1673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3107  -26.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294  -26.1717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0184  -22.4278    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:

   

   ALA1091435

   (3-Fluorophenyl)-[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: 375.40

Molecular Weight (Monoisotopic): 375.1482

AlogP: 2.61

#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: 5.24

CX LogP: 3.07

CX LogD: 2.30

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.78

Np Likeness Score: -0.60

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