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

ID: ALA4464508

PubChem CID: 155530723

Max Phase: Preclinical

Molecular Formula: C20H20N2O2S

Molecular Weight: 352.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c1sc3ccccc3c(=O)c1n2CCN(C)C

Standard InChI:  InChI=1S/C20H20N2O2S/c1-21(2)10-11-22-16-9-8-13(24-3)12-15(16)20-18(22)19(23)14-6-4-5-7-17(14)25-20/h4-9,12H,10-11H2,1-3H3

Standard InChI Key:  MSLMELFHKWHXGG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.2372   -2.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361   -3.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9441   -4.0226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9424   -2.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6510   -2.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6498   -3.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3560   -4.0202    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583   -2.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0691   -2.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0699   -3.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8471   -2.5389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3288   -3.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8486   -3.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1808   -4.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9928   -4.6897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4716   -4.0243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1368   -3.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583   -1.5617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0988   -1.7615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8980   -1.5908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1497   -0.8133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9489   -0.6426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6023   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3273   -5.4353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1402   -5.5185    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
  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
 15 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4464508

   ---

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: 352.46

Molecular Weight (Monoisotopic): 352.1245

AlogP: 3.94

#Rotatable Bonds: 4

Polar Surface Area: 34.47

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.37

CX LogP: 3.75

CX LogD: 2.74

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -1.15

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