N1-phenyl-N8-((2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)methoxy)octanediamide

ID: ALA3577298

PubChem CID: 122177622

Max Phase: Preclinical

Molecular Formula: C24H30N2O5

Molecular Weight: 426.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(C)C(=O)C(CONC(=O)CCCCCCC(=O)Nc2ccccc2)=C(C)C1=O

Standard InChI:  InChI=1S/C24H30N2O5/c1-16-17(2)24(30)20(18(3)23(16)29)15-31-26-22(28)14-10-5-4-9-13-21(27)25-19-11-7-6-8-12-19/h6-8,11-12H,4-5,9-10,13-15H2,1-3H3,(H,25,27)(H,26,28)

Standard InChI Key:  HXFDEOSGMWWMSA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4833   -9.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7815  -10.5187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7794  -12.0195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8218   -9.9205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0776  -12.7726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755  -14.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3737  -15.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3737  -16.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6728  -17.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9718  -16.5266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9719  -15.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6728  -14.2766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6729  -13.0766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0110  -17.1266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6727  -18.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3345  -17.1266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0111  -14.4266    0.0000 O   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
  1  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 26  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 24 28  1  0
 23 29  1  0
 22 30  2  0
 25 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3577298

   ---

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: 426.51

Molecular Weight (Monoisotopic): 426.2155

AlogP: 3.82

#Rotatable Bonds: 11

Polar Surface Area: 101.57

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.29

CX Basic pKa: ┄

CX LogP: 4.23

CX LogD: 4.18

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: -0.29

References

1. Daniel KB, Sullivan ED, Chen Y, Chan JC, Jennings PA, Fierke CA, Cohen SM..  (2015)  Dual-Mode HDAC Prodrug for Covalent Modification and Subsequent Inhibitor Release.,  58  (11): [PMID:25974739] [10.1021/acs.jmedchem.5b00539]

Source

Source(1):

• Scientific Literature