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

ID: ALA1093060

PubChem CID: 46884271

Max Phase: Preclinical

Molecular Formula: C21H25ClN2O4

Molecular Weight: 404.89

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H25ClN2O4/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:  GWQNBYJGRHHDOK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.4026  -10.1690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6878  -10.5819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713  -10.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9742   -9.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6896   -8.9289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1174  -10.5809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8315  -10.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6920   -8.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9788   -7.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562  -10.5799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2613   -8.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5453   -9.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644   -8.0978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455  -10.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1697  -10.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836  -10.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8778   -9.3205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620   -8.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880  -11.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4025  -11.8192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158  -11.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8282  -11.8169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8327  -12.6423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1185  -13.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3998  -12.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5429  -13.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5892   -8.9028    0.0000 Cl  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
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  6  9  1  0
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  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:

   

   ALA1093060

   (3-Chlorophenyl)-[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: 404.89

Molecular Weight (Monoisotopic): 404.1503

AlogP: 3.04

#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: 2.95

CX LogD: 2.77

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

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