4beta-N-(8''-aminoquinoline)-4-desoxy-podophyllotoxin

ID: ALA4476548

PubChem CID: 155538287

Max Phase: Preclinical

Molecular Formula: C31H28N2O7

Molecular Weight: 540.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@@H](Nc3cccc5cccnc35)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C31H28N2O7/c1-35-24-10-17(11-25(36-2)30(24)37-3)26-18-12-22-23(40-15-39-22)13-19(18)29(20-14-38-31(34)27(20)26)33-21-8-4-6-16-7-5-9-32-28(16)21/h4-13,20,26-27,29,33H,14-15H2,1-3H3/t20-,26+,27-,29+/m0/s1

Standard InChI Key:  SZQONOKRTGRBEI-SLFPAOIGSA-N

Molfile:  

 
     RDKit          2D

 42 48  0  0  0  0  0  0  0  0999 V2000
   32.6461   -6.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6443   -5.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3529   -5.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3518   -6.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0618   -6.6561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0642   -5.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9381   -6.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9393   -5.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1588   -5.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.6751   -5.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1568   -6.4952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7789   -5.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7756   -6.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5576   -6.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0443   -5.8383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.5629   -5.1703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0643   -4.1885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.0609   -7.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3535   -7.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3522   -8.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0599   -9.1054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7705   -8.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7683   -7.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4791   -9.1002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.4810   -9.9174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0600   -9.9226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3524  -10.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6438   -9.1025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.9368   -8.6927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8070   -7.2807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.7678   -7.0617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.7719   -4.6019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.7720   -3.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4761   -4.1898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1834   -3.7819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1839   -2.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7632   -2.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4714   -2.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4677   -1.7424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7567   -1.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0478   -1.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0550   -2.5689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0
  1  4  2  0
  3  2  2  0
  2  8  1  0
  3  4  1  0
  3  6  1  0
  4  5  1  0
  5 13  1  0
 12  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11  7  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  6 17  1  1
  5 18  1  6
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 22 24  1  0
 24 25  1  0
 21 26  1  0
 26 27  1  0
 20 28  1  0
 28 29  1  0
 14 30  2  0
 13 31  1  1
 12 32  1  6
 17 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 38  1  0
 37 33  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 37  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476548

   ---

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: 540.57

Molecular Weight (Monoisotopic): 540.1897

AlogP: 5.08

#Rotatable Bonds: 6

Polar Surface Area: 97.37

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 3.78

CX LogP: 3.75

CX LogD: 3.74

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.34

Np Likeness Score: 0.73

References

1. Zhao W, He L, Xiang TL, Tang YJ..  (2019)  Discover 4β-NH-(6-aminoindole)-4-desoxy-podophyllotoxin with nanomolar-potency antitumor activity by improving the tubulin binding affinity on the basis of a potential binding site nearby colchicine domain.,  170  [PMID:30878833] [10.1016/j.ejmech.2019.03.006]

Source

Source(1):

• Scientific Literature