N1-(4-(3-acetamidophenyl)thiazol-2-yl)-N8-(2-aminophenyl)octanediamide

ID: ALA4285537

PubChem CID: 145990601

Max Phase: Preclinical

Molecular Formula: C25H29N5O3S

Molecular Weight: 479.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1cccc(-c2csc(NC(=O)CCCCCCC(=O)Nc3ccccc3N)n2)c1

Standard InChI:  InChI=1S/C25H29N5O3S/c1-17(31)27-19-10-8-9-18(15-19)22-16-34-25(29-22)30-24(33)14-5-3-2-4-13-23(32)28-21-12-7-6-11-20(21)26/h6-12,15-16H,2-5,13-14,26H2,1H3,(H,27,31)(H,28,32)(H,29,30,33)

Standard InChI Key:  KNDBVKRRTUJIHZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 34 36  0  0  0  0  0  0  0  0999 V2000
   13.6961   -0.0278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4105   -0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4105   -1.2653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1250   -0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8395   -0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5539   -0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2684   -0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9829   -0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6974   -0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4118   -0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1263   -0.4403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4118    0.7972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8408   -0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9816   -0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2279   -0.1047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.6759   -0.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0884   -1.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8953   -1.2607    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.5552   -0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2697   -0.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2697    0.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5552    1.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8408    0.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8554   -0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5198    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6994    0.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2144   -0.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5500   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3705   -1.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1263    1.2097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3638    0.9620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8487    1.6295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5132    2.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6692    1.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
  1 14  1  0
 15 14  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  1  0
 19 13  2  0
 20 19  1  0
 21 20  2  0
 22 21  1  0
 23 22  2  0
 13 23  1  0
 24 16  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 24 29  1  0
 29 28  2  0
 23 30  1  0
 26 31  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4285537

   ---

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: 479.61

Molecular Weight (Monoisotopic): 479.1991

AlogP: 5.27

#Rotatable Bonds: 11

Polar Surface Area: 126.21

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.96

CX Basic pKa: 3.45

CX LogP: 4.03

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.22

Np Likeness Score: -1.50

References

1. Adhikari N, Amin SA, Trivedi P, Jha T, Ghosh B..  (2018)  HDAC3 is a potential validated target for cancer: An overview on the benzamide-based selective HDAC3 inhibitors through comparative SAR/QSAR/QAAR approaches.,  157  [PMID:30179749] [10.1016/j.ejmech.2018.08.081]

2. Sarkar R, Banerjee S, Amin SA, Adhikari N, Jha T..  (2020)  Histone deacetylase 3 (HDAC3) inhibitors as anticancer agents: A review.,  192  [PMID:32163814] [10.1016/j.ejmech.2020.112171]

Source

Source(1):

• Scientific Literature