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

ID: ALA1091048

PubChem CID: 46830168

Max Phase: Preclinical

Molecular Formula: C21H24BrNO4

Molecular Weight: 434.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c(C(=O)c2ccccc2Br)c(O)c1CN1CCCCC1

Standard InChI:  InChI=1S/C21H24BrNO4/c1-26-17-12-18(27-2)19(20(24)14-8-4-5-9-16(14)22)21(25)15(17)13-23-10-6-3-7-11-23/h4-5,8-9,12,25H,3,6-7,10-11,13H2,1-2H3

Standard InChI Key:  FNSSMPKCQXYKTF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.2236  -15.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2224  -16.7898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9372  -17.2027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6537  -16.7894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6508  -15.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9354  -15.5497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5076  -17.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7935  -16.7887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9330  -14.7247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6462  -14.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3688  -17.2007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3637  -15.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0797  -15.9534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3606  -14.7186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0795  -16.7761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7947  -17.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5086  -16.7706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5028  -15.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7870  -15.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7797  -14.7104    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   10.9370  -18.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2225  -18.4400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5092  -18.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7968  -18.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7923  -19.2631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5065  -19.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2252  -19.2675    0.0000 C   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
 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
 12 13  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091048

   (2-Bromophenyl)-[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: 434.33

Molecular Weight (Monoisotopic): 433.0889

AlogP: 4.39

#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: 5.68

CX Basic pKa: 8.13

CX LogP: 3.81

CX LogD: 3.79

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.68

Np Likeness Score: -0.20

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