2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluorooctanedioic acid hydroxyamide naph-thalen-2-ylamide

ID: ALA1934905

PubChem CID: 57336568

Max Phase: Preclinical

Molecular Formula: C18H10F12N2O3

Molecular Weight: 530.27

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)Nc1ccc2ccccc2c1

Standard InChI:  InChI=1S/C18H10F12N2O3/c19-13(20,11(33)31-10-6-5-8-3-1-2-4-9(8)7-10)15(23,24)17(27,28)18(29,30)16(25,26)14(21,22)12(34)32-35/h1-7,35H,(H,31,33)(H,32,34)

Standard InChI Key:  RRWQSJCXNLQODI-UHFFFAOYSA-N

Molfile:  

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    3.4173  -18.6748    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037  -19.9106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1308  -19.0867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4255  -17.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4241  -19.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1374  -18.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1426  -17.8509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8  7  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA1934905

   N-Hydroxy-N'-naphthalen-2-yl-perfluoro-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: 530.27

Molecular Weight (Monoisotopic): 530.0500

AlogP: 5.10

#Rotatable Bonds: 8

Polar Surface Area: 78.43

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.26

CX Basic pKa: ┄

CX LogP: 5.55

CX LogD: 5.50

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.25

Np Likeness Score: -0.58

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