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

ID: ALA4570313

PubChem CID: 155562655

Max Phase: Preclinical

Molecular Formula: C21H22N2O3S

Molecular Weight: 382.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c3sc4ccccc4c(=O)c3n(CCN(C)C)c2cc1OC

Standard InChI:  InChI=1S/C21H22N2O3S/c1-22(2)9-10-23-15-12-17(26-4)16(25-3)11-14(15)21-19(23)20(24)13-7-5-6-8-18(13)27-21/h5-8,11-12H,9-10H2,1-4H3

Standard InChI Key:  DKVWLOMOQOURQW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   12.8508  -15.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8496  -16.0779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5577  -16.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5559  -14.8495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2645  -15.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2633  -16.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9695  -16.4844    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   14.9719  -14.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6826  -15.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6834  -16.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4606  -15.0032    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9423  -15.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4621  -16.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7943  -17.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6064  -17.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0852  -16.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7504  -15.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9719  -14.0259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7124  -14.2257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5115  -14.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7633  -13.2776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5624  -13.1069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2159  -12.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9408  -17.8996    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7537  -17.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8983  -16.5699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3753  -15.9064    0.0000 C   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
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  7 10  1  0
  9  8  1  0
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  8 18  2  0
 11 19  1  0
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 20 21  1  0
 21 22  1  0
 21 23  1  0
 15 24  1  0
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 16 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4570313

   ---

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: 382.49

Molecular Weight (Monoisotopic): 382.1351

AlogP: 3.95

#Rotatable Bonds: 5

Polar Surface Area: 43.70

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.38

CX LogP: 3.59

CX LogD: 2.58

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.90

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