(1E,4E)-6-(1-(isopentylsulfonyl)heptyl)-5,8-dimethoxy-1,4-naphthoquinone-dioxime

ID: ALA4540173

PubChem CID: 155549779

Max Phase: Preclinical

Molecular Formula: C24H36N2O6S

Molecular Weight: 480.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCC(c1cc(OC)c2c(c1OC)/C(=N/O)C=C/C2=N\O)S(=O)(=O)CCC(C)C

Standard InChI:  InChI=1S/C24H36N2O6S/c1-6-7-8-9-10-21(33(29,30)14-13-16(2)3)17-15-20(31-4)22-18(25-27)11-12-19(26-28)23(22)24(17)32-5/h11-12,15-16,21,27-28H,6-10,13-14H2,1-5H3/b25-18+,26-19+

Standard InChI Key:  NCUHOFMSDSXALZ-XUWUHCBVSA-N

Molfile:  

 
     RDKit          2D

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   31.1199   -5.2790    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   30.4033   -5.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6905   -4.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4068   -4.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4040   -3.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6887   -2.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9756   -4.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9798   -3.2165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2693   -2.8015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5501   -3.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5459   -4.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2610   -4.4562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2580   -5.2812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5420   -5.6911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2746   -1.9765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5628   -1.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6854   -1.9788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3983   -1.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6903   -5.2817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1220   -4.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9756   -5.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8357   -4.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5509   -4.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8383   -5.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5522   -5.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2647   -4.0389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9797   -4.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6936   -4.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4086   -4.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2672   -5.6889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1156   -6.1040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.2685   -6.5138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9811   -5.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  7  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  8  1  0
  7  8  2  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
  9 15  2  0
 15 16  1  0
  6 17  1  0
 17 18  1  0
  3 19  1  0
  4 20  1  0
 20  1  1  0
 19 21  1  0
 20 22  1  0
 22 23  1  0
  1 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 25 30  1  0
  1 31  2  0
 30 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540173

   ---

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: 480.63

Molecular Weight (Monoisotopic): 480.2294

AlogP: 5.10

#Rotatable Bonds: 12

Polar Surface Area: 117.78

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.97

CX Basic pKa: ┄

CX LogP: 4.43

CX LogD: 2.14

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.24

Np Likeness Score: 0.28

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