NA

ID: ALA4878668

PubChem CID: 56849641

Max Phase: Preclinical

Molecular Formula: C24H21N3O9

Molecular Weight: 495.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@@H](n3cnc([N+](=O)[O-])c3)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O

Standard InChI:  InChI=1S/C24H21N3O9/c1-32-17-3-11(4-18(33-2)23(17)28)20-12-5-15-16(36-10-35-15)6-13(12)22(14-8-34-24(29)21(14)20)26-7-19(25-9-26)27(30)31/h3-7,9,14,20-22,28H,8,10H2,1-2H3/t14-,20+,21-,22+/m0/s1

Standard InChI Key:  TVXWPAGSCPVGDY-ITGOXPRASA-N

Molfile:  

 
     RDKit          2D

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    9.9475   -6.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7982   -7.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9475   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2200  -10.4575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3017   -5.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2282   -4.6956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5174   -5.9345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5091   -9.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9433   -7.5766    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.9785   -7.7927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.6459   -9.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0873   -6.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7982   -9.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5174   -6.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9350   -9.2145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2282   -7.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9350   -8.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9433   -5.1114    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2200   -9.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7331   -7.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2112   -6.3460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8915   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6371   -3.4324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8138   -3.4325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5596   -4.2154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1187   -2.7689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.7863   -2.0223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9314   -2.8543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 31 13  1  0
  1  9  1  1
 24 26  2  0
  8 20  1  0
 23 14  1  0
 22  1  1  0
 19  7  1  0
 17  5  1  0
 26 25  1  0
  4 28  1  0
  2 15  1  0
  5 18  1  0
 22 25  1  6
 29  1  1  0
 14 24  1  0
 12 15  1  0
 12 17  1  0
  1  3  1  0
 13  3  1  0
 21 16  1  0
 11 29  2  0
 20 25  2  0
  2 19  2  0
 31 29  1  0
 10  3  1  0
 28  8  2  0
 22 19  1  0
 15 18  2  0
  7 10  1  0
 28 24  1  0
 18 30  1  0
 16  8  1  0
  3 27  1  6
 10  6  1  1
 30  7  2  0
  6 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35  6  1  0
 36 37  2  0
 36 38  1  0
 33 36  1  0
M  CHG  2  36   1  38  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4878668

   (5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-(4-nitroimidazol-1-yl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one

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: 495.44

Molecular Weight (Monoisotopic): 495.1278

AlogP: 2.77

#Rotatable Bonds: 5

Polar Surface Area: 144.41

Molecular Species: NEUTRAL

HBA: 11

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.33

CX Basic pKa: 1.27

CX LogP: 2.61

CX LogD: 2.60

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.32

Np Likeness Score: 0.54

References

1. Xiao J, Gao M, Sun Z, Diao Q, Wang P, Gao F..  (2020)  Recent advances of podophyllotoxin/epipodophyllotoxin hybrids in anticancer activity, mode of action, and structure-activity relationship: An update (2010-2020).,  208  [PMID:32992133] [10.1016/j.ejmech.2020.112830]

Source

Source(1):

• Scientific Literature