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

ID: ALA2440717

PubChem CID: 72543939

Max Phase: Preclinical

Molecular Formula: C21H34N4O4

Molecular Weight: 406.53

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H34N4O4/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:  HOSWZQJRTLVKKS-ZRDIBKRKSA-N

Molfile:  

     RDKit          2D

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   38.6062  -14.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6050  -15.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3198  -16.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0363  -15.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0334  -14.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.3180  -14.5512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7463  -14.5451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4623  -14.9549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1752  -14.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8913  -14.9496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.6042  -14.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.1721  -13.7148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8916  -14.5516    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1772  -14.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4626  -14.5520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1774  -15.7893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7483  -14.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0337  -14.5523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3193  -14.9650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8902  -16.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.8895  -17.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1748  -17.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1741  -18.2652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4593  -18.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8882  -18.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8876  -19.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7452  -18.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6048  -14.5527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8904  -14.9653    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:

   

   ALA2440717

   (E)-3-[4-[2-(diethylamino)ethoxy]-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: 406.53

Molecular Weight (Monoisotopic): 406.2580

AlogP: 3.24

#Rotatable Bonds: 13

Polar Surface Area: 102.93

Molecular Species: BASE

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.73

CX Basic pKa: 9.08

CX LogP: 2.25

CX LogD: 0.94

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.17

Np Likeness Score: -1.02

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