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

ID: ALA2440721

PubChem CID: 72544177

Max Phase: Preclinical

Molecular Formula: C20H32N4O3S

Molecular Weight: 408.57

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H32N4O3S/c1-4-7-12-21-20(28)22-17-15-16(9-11-19(25)23-26)8-10-18(17)27-14-13-24(5-2)6-3/h8-11,15,26H,4-7,12-14H2,1-3H3,(H,23,25)(H2,21,22,28)/b11-9+

Standard InChI Key:  ANZLOLYTGQBPAB-PKNBQFBNSA-N

Molfile:  

     RDKit          2D

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   19.7142   -6.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4290   -6.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1454   -6.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1426   -5.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4272   -5.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8555   -5.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5715   -5.5281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2844   -5.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0004   -5.5227    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7134   -5.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2813   -4.2879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0008   -5.1248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2864   -5.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5718   -5.1251    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2866   -6.3624    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.8575   -5.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1429   -5.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4285   -5.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9994   -6.7764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9987   -7.6014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2839   -8.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2833   -8.8383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5685   -9.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9974   -9.2514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9968  -10.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8543   -8.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7139   -5.1258    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
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  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
M  END

Alternative Forms

1. Parent:

   

   ALA2440721

   (E)-3-[3-(butylcarbamothioylamino)-4-[2-(diethylamino)ethoxy]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: 408.57

Molecular Weight (Monoisotopic): 408.2195

AlogP: 3.01

#Rotatable Bonds: 12

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: 2.69

CX LogD: 1.38

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.14

Np Likeness Score: -1.19

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