5-(1-([1,1'-biphenyl]-3-ylmethyl)-1H-pyrazol-3-yl)-N-hydroxypentanamide

ID: ALA3335283

PubChem CID: 72195322

Max Phase: Preclinical

Molecular Formula: C21H23N3O2

Molecular Weight: 349.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCc1ccn(Cc2cccc(-c3ccccc3)c2)n1)NO

Standard InChI:  InChI=1S/C21H23N3O2/c25-21(23-26)12-5-4-11-20-13-14-24(22-20)16-17-7-6-10-19(15-17)18-8-2-1-3-9-18/h1-3,6-10,13-15,26H,4-5,11-12,16H2,(H,23,25)

Standard InChI Key:  UDRKLVCIAKBNQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   14.1200  -10.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9346   -9.9238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4147  -10.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2251  -10.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7053  -11.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6399   -9.3487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7857  -10.7593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2658  -11.4184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8108  -11.3503    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0677  -11.6847    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5198  -11.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9284  -10.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7268  -10.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5199  -11.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6431  -11.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9340  -11.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2290  -11.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2290  -10.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9340  -10.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6431  -10.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3521  -11.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0571  -11.3503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7662  -11.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7662  -12.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0571  -12.9847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3521  -12.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  2  0
  1  7  1  0
  7  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  9 13  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 15 21  1  0
 14 17  1  0
  9 14  1  0
  5 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335283

   N-hydroxy-5-[1-[(3-phenylphenyl)methyl]pyrazol-3-yl]pentanamide

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: 349.43

Molecular Weight (Monoisotopic): 349.1790

AlogP: 3.82

#Rotatable Bonds: 8

Polar Surface Area: 67.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.91

CX Basic pKa: 2.82

CX LogP: 3.81

CX LogD: 3.79

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.37

Np Likeness Score: -1.03

References

1. Yao Y, Liao C, Li Z, Wang Z, Sun Q, Liu C, Yang Y, Tu Z, Jiang S..  (2014)  Design, synthesis, and biological evaluation of 1, 3-disubstituted-pyrazole derivatives as new class I and IIb histone deacetylase inhibitors.,  86  [PMID:25218912] [10.1016/j.ejmech.2014.09.024]

Source

Source(1):

• Scientific Literature