(5R,5aS,8aR,9R)-5-[4-[(4-ethylphenoxy)methyl]triazol-1-yl]-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one

ID: ALA4877536

PubChem CID: 164628925

Max Phase: Preclinical

Molecular Formula: C33H33N3O8

Molecular Weight: 599.64

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCc1ccc(OCc2cn([C@H]3c4cc5c(cc4[C@@H](c4cc(OC)c(OC)c(OC)c4)[C@H]4C(=O)OC[C@@H]43)OCO5)nn2)cc1

Standard InChI:  InChI=1S/C33H33N3O8/c1-5-18-6-8-21(9-7-18)41-15-20-14-36(35-34-20)31-23-13-26-25(43-17-44-26)12-22(23)29(30-24(31)16-42-33(30)37)19-10-27(38-2)32(40-4)28(11-19)39-3/h6-14,24,29-31H,5,15-17H2,1-4H3/t24-,29+,30-,31-/m0/s1

Standard InChI Key:  XOQQTIWXPWPRMK-ONEAYSBLSA-N

Molfile:  

 
     RDKit          2D

 46 52  0  0  0  0  0  0  0  0999 V2000
   26.1483   -7.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7179   -8.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1483   -8.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4310   -8.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7179   -7.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4310   -6.8781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4310   -9.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9360   -8.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9966   -8.5323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9966   -6.8822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4228  -11.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4170   -7.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9360   -7.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7097  -10.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1358  -10.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835   -7.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2835   -8.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7097   -9.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1358   -9.7678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5082   -8.3831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4957   -7.0440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0231   -7.7197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1848   -9.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4310   -6.0531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.4228  -11.8283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.9966  -10.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8489  -10.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7097  -12.2429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2793  -10.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8489  -11.8200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1442   -8.9427    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.1442   -6.4718    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.0985   -5.5681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8435   -4.7835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.0185   -4.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7636   -5.5681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5359   -4.1194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8697   -3.3695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3871   -2.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7239   -1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2420   -1.2942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4247   -1.3798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0915   -2.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5754   -2.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9412   -0.7163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2740    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  1  1  0
  4  3  1  0
  5  6  1  0
  6  1  1  0
  4  7  1  6
  8  3  1  0
  9  2  2  0
 10  5  2  0
 11 15  1  0
 12 13  1  0
 13  1  1  0
 14 18  1  0
 15 19  2  0
 16 10  1  0
 17 16  2  0
 18  7  2  0
 19  7  1  0
 20 17  1  0
 21 16  1  0
 22 21  1  0
 23  8  2  0
  6 24  1  6
 25 11  1  0
 26 14  1  0
 27 15  1  0
 28 25  1  0
 29 26  1  0
 30 27  1  0
  3 31  1  1
  1 32  1  6
 12  8  1  0
  4  2  1  0
  9 17  1  0
 11 14  2  0
 20 22  1  0
 24 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 24  1  0
 35 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 39  1  0
 42 45  1  0
 45 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877536

   ---

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: 599.64

Molecular Weight (Monoisotopic): 599.2268

AlogP: 4.70

#Rotatable Bonds: 9

Polar Surface Area: 112.39

Molecular Species: NEUTRAL

HBA: 11

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.25

Np Likeness Score: 0.09

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