US9187406, compound 5

ID: ALA3906163

PubChem CID: 121595889

Max Phase: Preclinical

Molecular Formula: C24H28N2O2

Molecular Weight: 376.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)Cc1ccc(/C=C/C(=O)CC(=O)/C=C/c2ccc(N(C)C)cc2)cc1

Standard InChI:  InChI=1S/C24H28N2O2/c1-25(2)18-21-7-5-19(6-8-21)11-15-23(27)17-24(28)16-12-20-9-13-22(14-10-20)26(3)4/h5-16H,17-18H2,1-4H3/b15-11+,16-12+

Standard InChI Key:  NXFAPWYSRNCCLI-JOBJLJCHSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    3.6331   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8990    0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2003    1.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2024    2.6932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4990    0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8003    1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8024    2.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0990    0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4003    1.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6990    0.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0007    1.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2971    0.7228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2919   -0.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9903   -1.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6938   -0.7682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5875   -1.5348    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -15.5816   -2.7348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.6298   -0.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 21 24  1  0
 24 25  1  0
 24 26  1  0
  8 27  1  0
 27 28  2  0
 28  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3906163

   ---

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: 376.50

Molecular Weight (Monoisotopic): 376.2151

AlogP: 4.07

#Rotatable Bonds: 9

Polar Surface Area: 40.62

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.76

CX Basic pKa: 8.11

CX LogP: 4.97

CX LogD: 4.29

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -0.19

References

1.  (2015)  Curcumin analogues as zinc chelators and their uses, 

Source

Source(1):

• BindingDB Database