3,3'-(hexane-1,6-diylbis(azanediyl))bis(2-chloronaphthalene-1,4-dione)

ID: ALA4741600

Cas Number: 22272-10-2

PubChem CID: 267285

Max Phase: Preclinical

Molecular Formula: C26H22Cl2N2O4

Molecular Weight: 497.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C1C(Cl)=C(NCCCCCCNC2=C(Cl)C(=O)c3ccccc3C2=O)C(=O)c2ccccc21

Standard InChI:  InChI=1S/C26H22Cl2N2O4/c27-19-21(25(33)17-11-5-3-9-15(17)23(19)31)29-13-7-1-2-8-14-30-22-20(28)24(32)16-10-4-6-12-18(16)26(22)34/h3-6,9-12,29-30H,1-2,7-8,13-14H2

Standard InChI Key:  PLWFXPZIFGWMIB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   10.5504   -7.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5504   -8.5379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2625   -8.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2625   -7.2962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9745   -7.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9729   -8.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6839   -8.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3970   -8.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3946   -7.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6831   -7.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2637   -9.7713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2625   -6.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8365   -8.9514    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8347   -7.3024    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.1214   -8.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4075   -8.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6924   -8.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9785   -8.9555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2634   -8.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5496   -8.9577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8345   -8.5461    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1206   -8.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4063   -8.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4064  -10.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1244   -9.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915   -9.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6956   -8.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9843   -8.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2682   -8.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2680   -9.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9799  -10.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4065   -7.7220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048  -11.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8392  -10.1963    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  2  0
  4 12  2  0
  2 13  1  0
  1 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 25  2  0
 23 27  1  0
 26 24  1  0
 24 25  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 23 32  2  0
 24 33  2  0
 25 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4741600

   2,2'-(Hexane-1,6-diyldiimino)bis(3-chloronaphthalene-1,4-dione)

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: 497.38

Molecular Weight (Monoisotopic): 496.0957

AlogP: 4.79

#Rotatable Bonds: 9

Polar Surface Area: 92.34

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.48

Np Likeness Score: -0.10

References

1. Hu Y,Wang L,Han X,Zhou Y,Zhang T,Wang L,Hong T,Zhang W,Guo XX,Sun J,Qi Y,Yu J,Liu H,Wu F.  (2019)  Discovery of a Bioactive Inhibitor with a New Scaffold for Cystathionine γ-Lyase.,  62  (3): [PMID:30562026] [10.1021/acs.jmedchem.8b01720]

Source

Source(1):

• Scientific Literature