(3-fluorophenyl)(2-hydroxy-4,6-dimethoxy-3-((4-methylpiperazin-1-yl)methyl)phenyl)methanone

ID: ALA1091050

PubChem CID: 46830169

Max Phase: Preclinical

Molecular Formula: C21H25FN2O4

Molecular Weight: 388.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2cccc(F)c2)c(O)c1CN1CCN(C)CC1

Standard InChI:  InChI=1S/C21H25FN2O4/c1-23-7-9-24(10-8-23)13-16-17(27-2)12-18(28-3)19(21(16)26)20(25)14-5-4-6-15(22)11-14/h4-6,11-12,26H,7-10,13H2,1-3H3

Standard InChI Key:  OGGOGASSIIAXJW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -4.0598  -22.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609  -23.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3461  -23.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6297  -23.5602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6325  -22.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3479  -22.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7757  -23.9726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4899  -23.5595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3504  -21.4955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6371  -21.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145  -23.9716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9196  -22.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036  -22.7243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227  -21.4895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2038  -23.5469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4887  -23.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2252  -23.5414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2195  -22.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4963  -22.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3463  -24.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609  -25.2109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7741  -24.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4865  -25.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4910  -26.0340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7768  -26.4488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0581  -26.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2071  -26.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309  -22.2944    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  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
 24 27  1  0
  1  2  2  0
 18 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091050

   (3-Fluorophenyl)-[2-hydroxy-4,6-dimethoxy-3-[(4-methylpiperazin-1-yl)methyl]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: 388.44

Molecular Weight (Monoisotopic): 388.1798

AlogP: 2.53

#Rotatable Bonds: 6

Polar Surface Area: 62.24

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.10

CX Basic pKa: 7.10

CX LogP: 2.49

CX LogD: 2.31

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.77

Np Likeness Score: -0.50

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