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

ID: ALA4549107

PubChem CID: 155549373

Max Phase: Preclinical

Molecular Formula: C21H20Cl2N2OS

Molecular Weight: 419.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN(CC)CCn1c2ccc(Cl)cc2c2sc3cc(Cl)ccc3c(=O)c21

Standard InChI:  InChI=1S/C21H20Cl2N2OS/c1-3-24(4-2)9-10-25-17-8-6-13(22)11-16(17)21-19(25)20(26)15-7-5-14(23)12-18(15)27-21/h5-8,11-12H,3-4,9-10H2,1-2H3

Standard InChI Key:  NTOOTZDSMKPUSD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   13.8619   -9.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8608  -10.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5688  -11.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5671   -9.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2757   -9.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2745  -10.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9807  -11.2016    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.9830   -9.5603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6937   -9.9739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6946  -10.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4718   -9.7203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9535  -10.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4733  -11.0424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8055  -11.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6175  -11.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0963  -11.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7615  -10.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9830   -8.7431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7235   -8.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5227   -8.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7744   -7.9947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5736   -7.8240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2270   -7.3880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4788   -6.6105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8254   -7.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9520  -12.6167    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.1528  -11.2030    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
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 12 11  1  0
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 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
  2 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4549107

   ---

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: 419.38

Molecular Weight (Monoisotopic): 418.0673

AlogP: 6.02

#Rotatable Bonds: 5

Polar Surface Area: 25.24

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.92

CX LogP: 5.83

CX LogD: 4.30

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.40

Np Likeness Score: -1.34

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