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

ID: ALA2440711

PubChem CID: 72547525

Max Phase: Preclinical

Molecular Formula: C20H32N4O3S

Molecular Weight: 408.57

Molecule Type: Small molecule

Names and Identifiers

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

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

Standard InChI Key:  CHQRAVHDDOGPKV-PKNBQFBNSA-N

Molfile:  

     RDKit          2D

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   20.3311   -3.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0459   -3.9306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7624   -3.5173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7595   -2.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0441   -2.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4724   -2.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1885   -2.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9014   -2.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6174   -2.6760    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3303   -2.2608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8983   -1.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6177   -2.2781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9034   -2.6908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1888   -2.2784    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9035   -3.5158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4744   -2.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7598   -2.2788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0455   -2.6914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6163   -3.9297    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.6157   -4.7547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9009   -5.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9002   -5.9916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1854   -6.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6144   -6.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6137   -7.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4713   -5.9905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3309   -2.2791    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:

   

   ALA2440711

   (E)-3-[3-(butylcarbamoylamino)-4-[2-(diethylamino)ethylsulfanyl]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: 3.56

#Rotatable Bonds: 12

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: 2.39

CX LogD: 1.12

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.14

Np Likeness Score: -1.25

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