4alpha-[2-(4-isobutylphenyl)-propionate]-4-desoxypodophyllotoxin

ID: ALA4087564

PubChem CID: 137642707

Max Phase: Preclinical

Molecular Formula: C35H38O9

Molecular Weight: 602.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc([C@@H]2c3cc4c(cc3[C@H](OC(=O)C(C)c3ccc(CC(C)C)cc3)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

Standard InChI:  InChI=1S/C35H38O9/c1-18(2)11-20-7-9-21(10-8-20)19(3)34(36)44-32-24-15-27-26(42-17-43-27)14-23(24)30(31-25(32)16-41-35(31)37)22-12-28(38-4)33(40-6)29(13-22)39-5/h7-10,12-15,18-19,25,30-32H,11,16-17H2,1-6H3/t19?,25-,30+,31-,32-/m0/s1

Standard InChI Key:  DUPJGLIXVQPPPT-UBUFRXMASA-N

Molfile:  

     RDKit          2D

 46 51  0  0  0  0  0  0  0  0999 V2000
    9.1008   -6.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2219   -9.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8063   -9.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2219   -9.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5121  -10.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8063   -9.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5121   -8.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5121  -11.2219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9979  -10.2438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1005  -10.4006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1005   -8.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5121  -12.8604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4766   -9.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9979   -8.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8022  -12.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2178  -12.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3907   -9.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3907   -9.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8022  -11.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2178  -11.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6147  -10.2438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6147   -8.9231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1360   -9.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2496  -11.0238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5121   -7.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5203  -13.6776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0882  -12.8687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9318  -12.8687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8187  -14.0904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0923  -13.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6458  -12.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2219  -10.8051    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2219   -8.3618    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8085   -7.5404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1008   -7.9490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8085   -6.7191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5162   -6.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2234   -6.7220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9307   -6.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9311   -5.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2184   -5.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5141   -5.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6383   -5.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3465   -5.4942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0537   -5.0846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3476   -6.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  1  0
  4  2  1  0
  5  4  1  0
  6  7  1  0
  7  2  1  0
  5  8  1  6
  9  4  1  0
 10  3  2  0
 11  6  2  0
 12 16  1  0
 13 14  1  0
 14  2  1  0
 15 19  1  0
 16 20  2  0
 17 11  1  0
 18 17  2  0
 19  8  2  0
 20  8  1  0
 21 18  1  0
 22 17  1  0
 23 22  1  0
 24  9  2  0
  7 25  1  6
 26 12  1  0
 27 15  1  0
 28 16  1  0
 29 26  1  0
 30 27  1  0
 31 28  1  0
  4 32  1  1
  2 33  1  6
  9 13  1  0
  3  5  1  0
 18 10  1  0
 15 12  2  0
 23 21  1  0
 25 34  1  0
 34 35  2  0
 34 36  1  0
 36  1  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 37  1  0
 40 43  1  0
 43 44  1  0
 44 45  1  0
 44 46  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4087564

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 602.68

Molecular Weight (Monoisotopic): 602.2516

AlogP: 5.96

#Rotatable Bonds: 9

Polar Surface Area: 98.75

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.13

CX LogD: 6.13

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.27

Np Likeness Score: 1.06

References

1. Zhang L, Liu L, Zheng C, Wang Y, Nie X, Shi D, Chen Y, Wei G, Wang J..  (2017)  Synthesis and biological evaluation of novel podophyllotoxin-NSAIDs conjugates as multifunctional anti-MDR agents against resistant human hepatocellular carcinoma Bel-7402/5-FU cells.,  131  [PMID:28301815] [10.1016/j.ejmech.2017.03.011]

Source

Source(1):

• Scientific Literature