3-(4-(2-(diethylamino)ethoxy)-3-(3-pentylthioureido)phenyl)-N-hydroxyacrylamide

ID: ALA2440722

PubChem CID: 72544178

Max Phase: Preclinical

Molecular Formula: C21H34N4O3S

Molecular Weight: 422.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCNC(=S)Nc1cc(/C=C/C(=O)NO)ccc1OCCN(CC)CC

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

Standard InChI Key:  UORRAVDSYFMRGF-ZRDIBKRKSA-N

Molfile:  

     RDKit          2D

 29 29  0  0  0  0  0  0  0  0999 V2000
   33.4570   -5.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4559   -6.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1707   -6.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8871   -6.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8843   -5.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1689   -4.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5972   -4.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3132   -5.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0261   -4.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7421   -5.3643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.4550   -4.9492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.0230   -4.1295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7424   -4.9664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0281   -5.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3135   -4.9668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0283   -6.2041    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.5991   -5.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8846   -4.9671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1702   -5.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7411   -6.6181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7404   -7.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0256   -7.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0250   -8.6800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.3102   -9.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7391   -9.0931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7384   -9.9181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5960   -8.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4556   -4.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7412   -5.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  2  0
  1 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 24 27  1  0
 19 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2440722

   (E)-3-[4-[2-(diethylamino)ethoxy]-3-(pentylcarbamothioylamino)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: 3.40

#Rotatable Bonds: 13

Polar Surface Area: 85.86

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.74

CX Basic pKa: 9.09

CX LogP: 3.13

CX LogD: 1.82

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.13

Np Likeness Score: -1.08

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]

Source

Source(1):

• Scientific Literature