2,3-Dimethoxy-12-(2-(methylamino)ethyl)-[1,3]dioxolo[40,5':4,5]benzo[1,2-c]phenanthridin-13(12H)-one

ID: ALA4570069

PubChem CID: 146306862

Max Phase: Preclinical

Molecular Formula: C23H22N2O5

Molecular Weight: 406.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNCCn1c(=O)c2cc(OC)c(OC)cc2c2ccc3cc4c(cc3c21)OCO4

Standard InChI:  InChI=1S/C23H22N2O5/c1-24-6-7-25-22-14(5-4-13-8-20-21(9-15(13)22)30-12-29-20)16-10-18(27-2)19(28-3)11-17(16)23(25)26/h4-5,8-11,24H,6-7,12H2,1-3H3

Standard InChI Key:  ISACNBGFGVEWCJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    6.9819  -11.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6870  -11.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3963  -12.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1049  -12.7787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0993  -11.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6888  -12.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9807  -12.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9881  -14.0089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6913  -13.5979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2754  -13.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8644  -12.7816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5711  -14.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8160  -12.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5974  -12.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0727  -11.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5850  -11.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9922  -14.8261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1570  -12.3724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1576  -11.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1582  -14.0117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499  -13.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4007  -14.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1067  -13.5920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8161  -13.9976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5221  -13.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  2  0
  7  4  2  0
  3  2  2  0
  2  1  1  0
  3  4  1  0
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  5 18  2  0
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 15 16  1  0
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 18 19  1  0
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 20 21  1  0
 21 17  1  0
  9 22  2  0
 14 23  1  0
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 15 25  1  0
 25 26  1  0
 10 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4570069

   ---

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: 406.44

Molecular Weight (Monoisotopic): 406.1529

AlogP: 3.27

#Rotatable Bonds: 5

Polar Surface Area: 70.95

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.19

CX LogP: 2.54

CX LogD: 0.76

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: 0.22

References

1. Tang WL, Zhang Y, Hu DX, Yang H, Yu Q, Chen JW, Agama K, Pommier Y, An LK..  (2019)  Synthesis and biological evaluation of 5-aminoethyl benzophenanthridone derivatives as DNA topoisomerase IB inhibitors.,  178  [PMID:31176097] [10.1016/j.ejmech.2019.05.074]

Source

Source(1):

• Scientific Literature