2-(1-((2-(4-(1-Hydroxyethyl)phenoxy)phenyl)amino)ethylidene)-5-phenylcyclohexane-1,3-dione

ID: ALA4518432

PubChem CID: 155541372

Max Phase: Preclinical

Molecular Formula: C28H27NO4

Molecular Weight: 441.53

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(Nc1ccccc1Oc1ccc(C(C)O)cc1)=C1C(=O)CC(c2ccccc2)CC1=O

Standard InChI:  InChI=1S/C28H27NO4/c1-18(28-25(31)16-22(17-26(28)32)21-8-4-3-5-9-21)29-24-10-6-7-11-27(24)33-23-14-12-20(13-15-23)19(2)30/h3-15,19,22,29-30H,16-17H2,1-2H3/b28-18-

Standard InChI Key:  RHNIEYPBNVZJMF-VEILYXNESA-N

Molfile:  

 
     RDKit          2D

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   17.7677  -21.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7677  -22.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4730  -22.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1783  -22.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1783  -21.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4730  -20.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0588  -20.8405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0564  -20.0233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3523  -21.2511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4730  -20.0171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0606  -22.4738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8836  -22.4727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8810  -23.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5873  -23.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2966  -23.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2952  -22.4715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5883  -22.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6434  -20.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6450  -20.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9369  -19.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2294  -20.0327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2345  -20.8541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9431  -21.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9493  -22.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2447  -22.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5377  -22.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8336  -22.4951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8394  -23.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5552  -23.7162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2563  -23.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1354  -23.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4240  -23.3258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1427  -24.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  7  2  0
  7  8  1  0
  7  9  1  0
  6 10  2  0
  2 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  4 12  1  0
  9 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
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 31 32  1  0
 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4518432

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 441.53

Molecular Weight (Monoisotopic): 441.1940

AlogP: 5.93

#Rotatable Bonds: 6

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.74

CX Basic pKa: ┄

CX LogP: 4.76

CX LogD: 4.76

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -0.41

References

1. Bueno O, Gargantilla M, Estévez-Gallego J, Martins S, Díaz JF, Camarasa MJ, Liekens S, Pérez-Pérez MJ, Priego EM..  (2019)  Diphenyl ether derivatives occupy the expanded binding site of cyclohexanedione compounds at the colchicine site in tubulin by movement of the αT5 loop.,  171  [PMID:30921759] [10.1016/j.ejmech.2019.03.045]

Source

Source(1):

• Scientific Literature