N-(2-(Butylamino)-2-oxoethyl)-4-(dimethylamino)-N-(6-(hydroxyamino)-6-oxohexyl)-benzamide

ID: ALA4059953

PubChem CID: 137635601

Max Phase: Preclinical

Molecular Formula: C21H34N4O4

Molecular Weight: 406.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNC(=O)CN(CCCCCC(=O)NO)C(=O)c1ccc(N(C)C)cc1

Standard InChI:  InChI=1S/C21H34N4O4/c1-4-5-14-22-20(27)16-25(15-8-6-7-9-19(26)23-29)21(28)17-10-12-18(13-11-17)24(2)3/h10-13,29H,4-9,14-16H2,1-3H3,(H,22,27)(H,23,26)

Standard InChI Key:  DYRUOELLDRMZCM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.7116  -10.2355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1088  -10.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1316   -9.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8946  -10.2224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4974   -9.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4746  -10.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6566  -10.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2367  -11.6058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6339  -12.3209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4553  -12.3315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8714  -11.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9486   -9.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3686   -8.8465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3458  -10.2618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1856   -8.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9259  -10.9628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3231  -11.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1401  -11.6901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5373  -12.4043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3544  -12.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7516  -13.1316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7743  -11.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3317  -13.8327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2150  -13.0225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3979  -13.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6131  -13.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5828   -9.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3999   -9.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7971  -10.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
  9 24  1  0
 24 25  1  0
 24 26  1  0
 15 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4059953

   ---

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: 2.18

#Rotatable Bonds: 13

Polar Surface Area: 101.98

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.91

CX Basic pKa: 3.46

CX LogP: 1.68

CX LogD: 1.67

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.26

Np Likeness Score: -1.15

References

1. Krieger V, Hamacher A, Gertzen CGW, Senger J, Zwinderman MRH, Marek M, Romier C, Dekker FJ, Kurz T, Jung M, Gohlke H, Kassack MU, Hansen FK..  (2017)  Design, Multicomponent Synthesis, and Anticancer Activity of a Focused Histone Deacetylase (HDAC) Inhibitor Library with Peptoid-Based Cap Groups.,  60  (13): [PMID:28574690] [10.1021/acs.jmedchem.7b00197]

Source

Source(1):

• Scientific Literature