(1R,2R,3R)-N-Hydroxy-2-(1-oxo-2-(2,2,2-trifluoroethyl)-isoindolin-5-yl)-3-phenylcyclopropanecarboxamide

ID: ALA3109983

PubChem CID: 60148690

Max Phase: Preclinical

Molecular Formula: C20H17F3N2O3

Molecular Weight: 390.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)[C@@H]1[C@H](c2ccccc2)[C@H]1c1ccc2c(c1)CN(CC(F)(F)F)C2=O

Standard InChI:  InChI=1S/C20H17F3N2O3/c21-20(22,23)10-25-9-13-8-12(6-7-14(13)19(25)27)16-15(17(16)18(26)24-28)11-4-2-1-3-5-11/h1-8,15-17,28H,9-10H2,(H,24,26)/t15-,16-,17-/m1/s1

Standard InChI Key:  ILEGKQBIIBREPC-BRWVUGGUSA-N

Molfile:  

     RDKit          2D

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    7.1398   -6.8083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9606   -6.8016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5378   -5.2732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8236   -4.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2453   -4.8570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6748   -7.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6815   -8.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3957   -8.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1033   -8.0156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0966   -7.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3824   -6.7901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9596   -5.2617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4322   -7.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7210   -6.8160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0139   -7.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434   -8.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7410   -8.4630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0170   -8.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4030   -8.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7476   -9.3721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -9.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6023   -8.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3448  -10.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592  -10.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3563  -11.4985    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.5763  -10.7808    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.1632  -11.4902    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  3  1  0
  4  5  2  0
  4  6  1  0
  1  4  1  6
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  3  7  1  6
  6 13  1  0
  2 14  1  1
 14 15  2  0
 15 16  1  0
 16 19  2  0
 18 17  2  0
 17 14  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 20 23  2  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3109983

   3beta-[1-Oxo-2-(2,2,2-trifluoroethyl)isoindoline-5-yl]-2alpha-phenylcyclopropane-1alpha-carbohydroxamic acid

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: 390.36

Molecular Weight (Monoisotopic): 390.1191

AlogP: 3.21

#Rotatable Bonds: 4

Polar Surface Area: 69.64

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: 2.58

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.62

Np Likeness Score: -0.17

References

1. Bürli RW, Luckhurst CA, Aziz O, Matthews KL, Yates D, Lyons KA, Beconi M, McAllister G, Breccia P, Stott AJ, Penrose SD, Wall M, Lamers M, Leonard P, Müller I, Richardson CM, Jarvis R, Stones L, Hughes S, Wishart G, Haughan AF, O'Connell C, Mead T, McNeil H, Vann J, Mangette J, Maillard M, Beaumont V, Munoz-Sanjuan I, Dominguez C..  (2013)  Design, synthesis, and biological evaluation of potent and selective class IIa histone deacetylase (HDAC) inhibitors as a potential therapy for Huntington's disease.,  56  (24): [PMID:24261862] [10.1021/jm4011884]

Source

Source(1):

• Scientific Literature