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

ID: ALA1093732

PubChem CID: 46884329

Max Phase: Preclinical

Molecular Formula: C21H24ClNO4

Molecular Weight: 389.88

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H24ClNO4/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:  YIDAOOAGFQVSJK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   10.5152  -10.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141  -11.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2289  -11.7985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9453  -11.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9425  -10.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2271  -10.1455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7993  -11.7976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0851  -11.3845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2246   -9.3205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9379   -8.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6605  -11.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6554  -10.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3714  -10.5493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6523   -9.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3712  -11.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0863  -11.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8002  -11.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7945  -10.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0787  -10.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2287  -12.6235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141  -13.0359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8009  -12.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0885  -13.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0840  -13.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7982  -14.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5169  -13.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5059  -10.1194    0.0000 Cl  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:

   

   ALA1093732

   (3-Chlorophenyl)-[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: 389.88

Molecular Weight (Monoisotopic): 389.1394

AlogP: 4.28

#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: 8.15

CX LogP: 3.65

CX LogD: 3.62

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.34

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