3-(4-(2-(diethylamino)ethylthio)-3-(3-pentylureido)phenyl)-N-hydroxyacrylamide

ID: ALA2440712

PubChem CID: 72547526

Max Phase: Preclinical

Molecular Formula: C21H34N4O3S

Molecular Weight: 422.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCNC(=O)Nc1cc(/C=C/C(=O)NO)ccc1SCCN(CC)CC

Standard InChI:  InChI=1S/C21H34N4O3S/c1-4-7-8-13-22-21(27)23-18-16-17(10-12-20(26)24-28)9-11-19(18)29-15-14-25(5-2)6-3/h9-12,16,28H,4-8,13-15H2,1-3H3,(H,24,26)(H2,22,23,27)/b12-10+

Standard InChI Key:  HWENGHCULNSUQK-ZRDIBKRKSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   11.4386   -0.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4003   -1.4841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0990   -0.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8003   -1.4887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4990   -0.7409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2003   -1.4932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990   -0.7455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969    0.4545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003   -1.4977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039    3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070    5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688    5.8520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078    5.9988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6103    7.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0031   -3.0008    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -3.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3070   -5.2502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6078   -5.9988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6109   -7.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6510   -8.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9078   -5.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9472   -5.8485    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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 12 19  2  0
 19 20  1  0
 20 21  2  0
 21 10  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2440712

   (E)-3-[4-[2-(diethylamino)ethylsulfanyl]-3-(pentylcarbamoylamino)phenyl]-N-hydroxyprop-2-enamide

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: 422.60

Molecular Weight (Monoisotopic): 422.2352

AlogP: 3.95

#Rotatable Bonds: 13

Polar Surface Area: 93.70

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.70

CX Basic pKa: 9.02

CX LogP: 2.83

CX LogD: 1.56

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.13

Np Likeness Score: -1.14

References

1. Ning C, Bi Y, He Y, Huang W, Liu L, Li Y, Zhang S, Liu X, Yu N..  (2013)  Design, synthesis and biological evaluation of di-substituted cinnamic hydroxamic acids bearing urea/thiourea unit as potent histone deacetylase inhibitors.,  23  (23): [PMID:24119555] [10.1016/j.bmcl.2013.09.051]

2.  (2014)  Histone deacetylase inhibitors, process for preparation and uses thereof, 

Source

Source(2):

• Scientific Literature
• BindingDB Database