2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-N1,N8-diphenyloctanediamide

ID: ALA1934910

PubChem CID: 57401090

Max Phase: Preclinical

Molecular Formula: C20H12F12N2O2

Molecular Weight: 540.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccccc1)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)Nc1ccccc1

Standard InChI:  InChI=1S/C20H12F12N2O2/c21-15(22,13(35)33-11-7-3-1-4-8-11)17(25,26)19(29,30)20(31,32)18(27,28)16(23,24)14(36)34-12-9-5-2-6-10-12/h1-10H,(H,33,35)(H,34,36)

Standard InChI Key:  MOKUJYDZSIDWRN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.2042  -25.5208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.6208  -26.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0332  -25.5183    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.3125  -27.3625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.9042  -26.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4913  -27.3599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.7750  -25.5208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.1917  -26.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6040  -25.5183    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.8833  -27.3625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4750  -26.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0621  -27.3599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3458  -25.5208    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.7625  -26.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1748  -25.5183    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542  -27.3625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0458  -26.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6330  -27.3599    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.6208  -26.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3353  -26.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3353  -25.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3366  -26.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0511  -26.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3366  -27.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9064  -26.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9113  -25.4156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1977  -25.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822  -25.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4849  -26.2450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1991  -26.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7655  -26.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7639  -27.4802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4775  -27.8927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1930  -27.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1903  -26.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4761  -26.2422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20 21  2  0
 17 14  1  0
 14 11  1  0
 11  8  1  0
  8  5  1  0
  5  2  1  0
 14 13  1  0
  2 22  1  0
 15 14  1  0
 22 23  1  0
  9  8  1  0
 22 24  2  0
  5  4  1  0
 19 25  1  0
  6  5  1  0
 25 26  2  0
 17 16  1  0
 26 27  1  0
 18 17  1  0
 27 28  2  0
 28 29  1  0
 11 10  1  0
 29 30  2  0
 30 25  1  0
 12 11  1  0
 23 31  1  0
  2  1  1  0
 31 32  2  0
  3  2  1  0
 32 33  1  0
 19 20  1  0
 33 34  2  0
 20 17  1  0
 34 35  1  0
  8  7  1  0
 35 36  2  0
 36 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1934910

   N,N'-Diphenylperfluoro-octanediamide

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: 540.30

Molecular Weight (Monoisotopic): 540.0707

AlogP: 6.08

#Rotatable Bonds: 9

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.12

CX Basic pKa: ┄

CX LogP: 6.81

CX LogD: 6.81

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.38

Np Likeness Score: -0.57

References

1. Henkes LM, Haus P, Jäger F, Ludwig J, Meyer-Almes FJ..  (2012)  Synthesis and biochemical analysis of 2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-N-hydroxy-octanediamides as inhibitors of human histone deacetylases.,  20  (2): [PMID:22182579] [10.1016/j.bmc.2011.11.041]

2. Meyners C, Wolff B, Kleinschek A, Krämer A, Meyer-Almes FJ..  (2017)  Perfluorinated hydroxamic acids are potent and selective inhibitors of HDAC-like enzymes from Pseudomonas aeruginosa.,  27  (7): [PMID:28259626] [10.1016/j.bmcl.2017.02.050]

Source

Source(1):

• Scientific Literature