2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-N1-hydroxy-N8-m-tolyloctanediamide

ID: ALA4098910

PubChem CID: 137658785

Max Phase: Preclinical

Molecular Formula: C15H10F12N2O3

Molecular Weight: 494.23

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cccc(NC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)NO)c1

Standard InChI:  InChI=1S/C15H10F12N2O3/c1-6-3-2-4-7(5-6)28-8(30)10(16,17)12(20,21)14(24,25)15(26,27)13(22,23)11(18,19)9(31)29-32/h2-5,32H,1H3,(H,28,30)(H,29,31)

Standard InChI Key:  KNFFIUMUAMRWOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   28.4820   -1.3867    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.6966   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2756   -1.5971    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.3912   -3.2935    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.9867   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5778   -3.2909    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.8683   -1.4693    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.2810   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6894   -1.4668    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.7816   -3.3761    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.5711   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9937   -3.1642    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.4526   -1.4693    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.8653   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2738   -1.4668    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.5599   -3.2935    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   25.1555   -2.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7465   -3.2909    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.7439   -2.5919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4517   -2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4517   -1.3661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4056   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1133   -2.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.4056   -3.4091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0362   -2.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0412   -1.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3343   -0.9565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6256   -1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6282   -2.1866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3357   -2.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8210   -2.5919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9220   -2.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
  6  5  1  0
  8  7  1  0
  9  8  1  0
 11 10  1  0
 12 11  1  0
 14 13  1  0
 15 14  1  0
 17 16  1  0
 18 17  1  0
 19 20  1  0
 20 17  1  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
  2 22  1  0
 22 23  1  0
 22 24  2  0
 19 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
 23 31  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098910

   ---

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: 494.23

Molecular Weight (Monoisotopic): 494.0500

AlogP: 4.25

#Rotatable Bonds: 8

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.26

CX Basic pKa: ┄

CX LogP: 5.08

CX LogD: 5.02

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.77

References

1. 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