N-(2-(butylamino)-2-oxoethyl)-4-(dimethylamino)-N-(4-(hydroxycarbamoyl)benzyl)benzamide

ID: ALA4278449

PubChem CID: 145979587

Max Phase: Preclinical

Molecular Formula: C23H30N4O4

Molecular Weight: 426.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCNC(=O)CN(Cc1ccc(C(=O)NO)cc1)C(=O)c1ccc(N(C)C)cc1

Standard InChI:  InChI=1S/C23H30N4O4/c1-4-5-14-24-21(28)16-27(15-17-6-8-18(9-7-17)22(29)25-31)23(30)19-10-12-20(13-11-19)26(2)3/h6-13,31H,4-5,14-16H2,1-3H3,(H,24,28)(H,25,29)

Standard InChI Key:  IHUFKRMPDWCPHH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    6.7755   -6.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7743   -7.2291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4824   -7.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1921   -7.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1892   -6.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4806   -6.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9004   -7.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9017   -8.4533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6075   -7.2264    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3158   -7.6339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0677   -6.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3601   -6.4099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6523   -6.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6521   -5.1843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3597   -4.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3603   -7.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0681   -7.6355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6527   -7.6358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9463   -7.2236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2392   -7.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2390   -8.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9518   -8.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6560   -8.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9489   -4.7721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9400   -3.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -3.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6449   -2.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3538   -2.3313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5319   -8.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8236   -8.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5332   -9.6767    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
  4  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 24  1  0
 14 15  2  0
 12 16  1  0
 16 17  2  0
 16 18  1  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
 25 24  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 21 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4278449

   ---

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: 426.52

Molecular Weight (Monoisotopic): 426.2267

AlogP: 2.43

#Rotatable Bonds: 10

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: 9.05

CX Basic pKa: 3.45

CX LogP: 2.17

CX LogD: 2.16

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -1.44

References

1. Diedrich D, Stenzel K, Hesping E, Antonova-Koch Y, Gebru T, Duffy S, Fisher G, Schöler A, Meister S, Kurz T, Avery VM, Winzeler EA, Held J, Andrews KT, Hansen FK..  (2018)  One-pot, multi-component synthesis and structure-activity relationships of peptoid-based histone deacetylase (HDAC) inhibitors targeting malaria parasites.,  158  [PMID:30245402] [10.1016/j.ejmech.2018.09.018]

Source

Source(1):

• Scientific Literature