(E)-N-(1-(butylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl)-4-(3-(hydroxyamino)-3-oxoprop-1-en-1-yl)benzamide

ID: ALA4553537

PubChem CID: 155510418

Max Phase: Preclinical

Molecular Formula: C25H28N4O4

Molecular Weight: 448.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCNC(=O)C(Cc1c[nH]c2ccccc12)NC(=O)c1ccc(/C=C/C(=O)NO)cc1

Standard InChI:  InChI=1S/C25H28N4O4/c1-2-3-14-26-25(32)22(15-19-16-27-21-7-5-4-6-20(19)21)28-24(31)18-11-8-17(9-12-18)10-13-23(30)29-33/h4-13,16,22,27,33H,2-3,14-15H2,1H3,(H,26,32)(H,28,31)(H,29,30)/b13-10+

Standard InChI Key:  DYKJZQRPCQBIFI-JLHYYAGUSA-N

Molfile:  

 
     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
   23.8292   -9.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8281  -10.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5361  -10.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2458  -10.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2429   -9.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   23.1200  -10.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4126  -10.2821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.1194  -11.5085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7046  -10.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9972  -10.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7040  -11.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9959  -11.9154    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.4113  -11.9165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2892  -10.6890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4060  -11.6764    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2054  -11.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9979  -10.9683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5435  -10.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2936   -9.5932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4985   -9.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9537  -10.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2066  -10.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9491   -9.0488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6583   -9.4548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3645   -9.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0737   -9.4494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3614   -8.2263    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7799   -9.0382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9953  -12.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6998  -13.1376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7013  -13.9547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4098  -14.3620    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
  2  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 11 15  1  0
 15 19  1  0
 18 16  1  0
 16 17  1  0
 17 15  2  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  5 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 27 29  1  0
 13 30  1  0
 31 30  1  0
 31 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553537

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 448.52

Molecular Weight (Monoisotopic): 448.2111

AlogP: 2.94

#Rotatable Bonds: 10

Polar Surface Area: 123.32

Molecular Species: NEUTRAL

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: ┄

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.14

Np Likeness Score: -0.32

References

1. Zhang Q, Lv J, He F, Yu C, Qu Y, Zhang X, Xu A, Wu J..  (2019)  Design, synthesis and activity evaluation of indole-based double - Branched HDAC1 inhibitors.,  27  (8): [PMID:30879863] [10.1016/j.bmc.2019.03.008]

Source

Source(1):

• Scientific Literature