2,2,3,3,4,4,5,5,6,6,7,7-dodecafluoro-N1-(4-fluorophenyl)-N8-hydroxyoctanediamide

ID: ALA4079958

PubChem CID: 137649646

Max Phase: Preclinical

Molecular Formula: C14H7F13N2O3

Molecular Weight: 498.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(=O)Nc1ccc(F)cc1

Standard InChI:  InChI=1S/C14H7F13N2O3/c15-5-1-3-6(4-2-5)28-7(30)9(16,17)11(20,21)13(24,25)14(26,27)12(22,23)10(18,19)8(31)29-32/h1-4,32H,(H,28,30)(H,29,31)

Standard InChI Key:  LNTUQEQVBMRDNL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 32  0  0  0  0  0  0  0  0999 V2000
   17.5737  -10.5286    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.7884  -11.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3673  -10.7389    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.4829  -12.4353    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.0785  -11.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6695  -12.4327    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9600  -10.6111    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.3727  -11.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7811  -10.6086    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.8733  -12.5179    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.6628  -11.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0854  -12.3060    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.5444  -10.6111    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.9571  -11.3210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3655  -10.6086    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.6517  -12.4353    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.2472  -11.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382  -12.4327    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.8357  -11.7337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5434  -11.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5434  -10.5079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4973  -11.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2051  -11.3251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4973  -12.5509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1280  -11.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1329  -10.5069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4260  -10.0983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7173  -10.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7200  -11.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4274  -11.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9128  -11.7337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0091  -10.0993    0.0000 F   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
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4079958

   ---

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: 498.20

Molecular Weight (Monoisotopic): 498.0249

AlogP: 4.08

#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: 4.71

CX LogD: 4.65

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.29

Np Likeness Score: -0.75

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