5-(1-(4-(1H-indol-1-yl)benzyl)-1H-pyrazol-3-yl)-N-hydroxypentanamide

ID: ALA3335298

PubChem CID: 118714375

Max Phase: Preclinical

Molecular Formula: C23H24N4O2

Molecular Weight: 388.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCc1ccn(Cc2ccc(-n3ccc4ccccc43)cc2)n1)NO

Standard InChI:  InChI=1S/C23H24N4O2/c28-23(25-29)8-4-2-6-20-14-15-26(24-20)17-18-9-11-21(12-10-18)27-16-13-19-5-1-3-7-22(19)27/h1,3,5,7,9-16,29H,2,4,6,8,17H2,(H,25,28)

Standard InChI Key:  VUALYNHSKFMOKH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   13.6674  -11.9223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4589  -11.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0372  -12.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8246  -12.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4311  -12.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0931  -11.3439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4583  -12.7097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0367  -13.2880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5349  -12.3717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8716  -12.8518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.2083  -12.3717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4630  -11.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2802  -11.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3080  -12.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9186  -12.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7478  -11.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3543  -10.7281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1315  -10.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3022  -11.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6958  -12.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7380  -10.4349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6539   -9.6245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4012   -9.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9449   -9.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7621   -9.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1707  -10.6057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7621  -11.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9449  -11.3148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5363  -10.6057    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
 14 15  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  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 21 29  1  0
 24 29  2  0
 18 21  1  0
  9 14  1  0
  5 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3335298

   ---

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: 388.47

Molecular Weight (Monoisotopic): 388.1899

AlogP: 4.09

#Rotatable Bonds: 8

Polar Surface Area: 72.08

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.91

CX Basic pKa: 2.82

CX LogP: 4.14

CX LogD: 4.13

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.27

Np Likeness Score: -1.21

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