(1E,4E)-6-(1-(hexylthio)nonyl)-5,8-dimethoxy-1,4-naphthoquinone-dioxime

ID: ALA4483767

PubChem CID: 155540599

Max Phase: Preclinical

Molecular Formula: C27H42N2O4S

Molecular Weight: 490.71

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCCC(SCCCCCC)c1cc(OC)c2c(c1OC)/C(=N/O)C=C/C2=N\O

Standard InChI:  InChI=1S/C27H42N2O4S/c1-5-7-9-11-12-13-15-24(34-18-14-10-8-6-2)20-19-23(32-3)25-21(28-30)16-17-22(29-31)26(25)27(20)33-4/h16-17,19,24,30-31H,5-15,18H2,1-4H3/b28-21+,29-22+

Standard InChI Key:  IWPPBHOCBYLDEL-XXGIQBRXSA-N

Molfile:  

 
     RDKit          2D

 34 35  0  0  0  0  0  0  0  0999 V2000
    5.3412  -27.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0576  -27.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0548  -26.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3394  -25.9405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264  -27.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6306  -26.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9201  -25.9383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2009  -26.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1968  -27.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9118  -27.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9088  -28.4180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928  -28.8278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9253  -25.1133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2136  -24.6963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3362  -25.1155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0491  -24.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3410  -28.4185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7727  -27.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7740  -28.4165    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6264  -28.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865  -27.1779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2017  -27.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4891  -28.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2029  -28.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9154  -27.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6305  -27.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3443  -27.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0594  -27.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7733  -27.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4883  -27.5825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9180  -28.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6319  -28.4120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3469  -28.8234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0607  -28.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 13  2  0
 13 14  1  0
  4 15  1  0
 15 16  1  0
  1 17  1  0
  2 18  1  0
 18 19  1  0
 17 20  1  0
 18 21  1  0
 21 22  1  0
 19 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 24 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4483767

   ---

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: 490.71

Molecular Weight (Monoisotopic): 490.2865

AlogP: 7.74

#Rotatable Bonds: 16

Polar Surface Area: 83.64

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.22

CX Basic pKa: ┄

CX LogP: 7.68

CX LogD: 5.60

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.14

Np Likeness Score: 0.32

References

1. Huang G, Dong JY, Zhang QJ, Meng QQ, Zhao HR, Zhu BQ, Li SS..  (2019)  Discovery and synthesis of sulfur-containing 6-substituted 5,8-dimethoxy-1,4-naphthoquinone oxime derivatives as new and potential anti-MDR cancer agents.,  165  [PMID:30677614] [10.1016/j.ejmech.2019.01.005]

Source

Source(1):

• Scientific Literature