2,2,3,3,4,4,5,5,6,6,7,7-Dodecafluorooctanedioic acid hydroxyamide phenan-thren-9-ylamide

ID: ALA1934908

PubChem CID: 57336571

Max Phase: Preclinical

Molecular Formula: C22H12F12N2O3

Molecular Weight: 580.33

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)Nc1cc2ccccc2c2ccccc12

Standard InChI:  InChI=1S/C22H12F12N2O3/c23-17(24,19(27,28)21(31,32)22(33,34)20(29,30)18(25,26)16(38)36-39)15(37)35-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)14/h1-9,39H,(H,35,37)(H,36,38)

Standard InChI Key:  HJRQSMKNJOBECK-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1934908

   N-Hydroxy-N'-phenanthren-9-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: 580.33

Molecular Weight (Monoisotopic): 580.0656

AlogP: 6.25

#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: 6.54

CX LogD: 6.49

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.13

Np Likeness Score: -0.43

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