11-[2-(Diethylamino)ethyl]-7-chloro-2,3-dimethoxybenzothiopyrano[3,2-b]indol-10(11H)-one

ID: ALA4568842

PubChem CID: 155560650

Max Phase: Preclinical

Molecular Formula: C23H25ClN2O3S

Molecular Weight: 444.98

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(CC)CCn1c2cc(OC)c(OC)cc2c2sc3cc(Cl)ccc3c(=O)c21

Standard InChI:  InChI=1S/C23H25ClN2O3S/c1-5-25(6-2)9-10-26-17-13-19(29-4)18(28-3)12-16(17)23-21(26)22(27)15-8-7-14(24)11-20(15)30-23/h7-8,11-13H,5-6,9-10H2,1-4H3

Standard InChI Key:  PDUBUEOXKXWQQG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.4289  -10.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1370  -10.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1352   -9.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8438   -9.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8426  -10.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5488  -10.6815    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.5512   -9.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2619   -9.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2627  -10.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0399   -9.2003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5216   -9.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0414  -10.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3736  -11.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1857  -11.3511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6645  -10.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3297   -9.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5512   -8.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2917   -8.4228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0908   -8.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3426   -7.4747    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1417   -7.3040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7952   -6.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0469   -6.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3935   -6.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5201  -12.0967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3330  -12.1799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4776  -10.7670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9546  -10.1035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7209  -10.6830    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
 10 13  1  0
 12 11  1  0
 11  9  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  8 18  2  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 22 25  1  0
 15 26  1  0
 26 27  1  0
 16 28  1  0
 28 29  1  0
  2 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4568842

   ---

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: 444.98

Molecular Weight (Monoisotopic): 444.1274

AlogP: 5.38

#Rotatable Bonds: 7

Polar Surface Area: 43.70

Molecular Species: BASE

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.93

CX LogP: 4.91

CX LogD: 3.38

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.38

Np Likeness Score: -1.07

References

1. Salerno S, La Pietra V, Hyeraci M, Taliani S, Robello M, Barresi E, Milite C, Simorini F, García-Argáez AN, Marinelli L, Novellino E, Da Settimo F, Marini AM, Dalla Via L..  (2019)  Benzothiopyranoindole- and pyridothiopyranoindole-based antiproliferative agents targeting topoisomerases.,  165  [PMID:30660826] [10.1016/j.ejmech.2019.01.015]

Source

Source(1):

• Scientific Literature