rac-4-(1-(4-(1H-pyrazol-4-yl)phenyl)cyclohexane-1-carboxamido)-N-hydroxybenzamide

ID: ALA4639966

PubChem CID: 156014913

Max Phase: Preclinical

Molecular Formula: C23H24N4O3

Molecular Weight: 404.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NO)c1ccc(NC(=O)C2(c3ccc(-c4cn[nH]c4)cc3)CCCCC2)cc1

Standard InChI:  InChI=1S/C23H24N4O3/c28-21(27-30)17-6-10-20(11-7-17)26-22(29)23(12-2-1-3-13-23)19-8-4-16(5-9-19)18-14-24-25-15-18/h4-11,14-15,30H,1-3,12-13H2,(H,24,25)(H,26,29)(H,27,28)

Standard InChI Key:  CWMHAEARRTUTJU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.1855  -19.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4678  -19.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4632  -20.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1745  -21.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922  -20.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8985  -19.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7582  -19.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4757  -19.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4729  -18.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7564  -17.8752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9067  -19.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6227  -19.5252    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376  -19.1091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0483  -19.5243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7627  -19.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7618  -18.2825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0407  -17.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3293  -18.2866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4761  -17.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1928  -18.2784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9071  -17.8657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9054  -18.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4737  -17.0443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0423  -19.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0390  -18.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3266  -17.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391  -17.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4353  -16.8937    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0260  -17.6059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5769  -18.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 24  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 25  1  0
  8  1  1  0
  1 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 11 22  2  0
 19 23  2  0
 24 25  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  1  0
 30 26  2  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4639966

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 404.47

Molecular Weight (Monoisotopic): 404.1848

AlogP: 4.04

#Rotatable Bonds: 5

Polar Surface Area: 107.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.20

CX Basic pKa: 2.28

CX LogP: 3.81

CX LogD: 3.81

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.21

References

1. Tng J, Lim J, Wu KC, Lucke AJ, Xu W, Reid RC, Fairlie DP..  (2020)  Achiral Derivatives of Hydroxamate AR-42 Potently Inhibit Class I HDAC Enzymes and Cancer Cell Proliferation.,  63  (11): [PMID:32383881] [10.1021/acs.jmedchem.0c00230]

Source

Source(1):

• Scientific Literature