Frugoside

ID: ALA4781168

PubChem CID: 154496583

Max Phase: Preclinical

Molecular Formula: C29H44O9

Molecular Weight: 536.66

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(CO)[C@@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H](C5=CC(=O)OC5)CC[C@]43O)C2)[C@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C29H44O9/c1-15-23(32)24(33)25(34)26(37-15)38-18-5-9-28(14-30)17(12-18)3-4-21-20(28)6-8-27(2)19(7-10-29(21,27)35)16-11-22(31)36-13-16/h11,15,17-21,23-26,30,32-35H,3-10,12-14H2,1-2H3/t15-,17+,18+,19-,20+,21-,23-,24-,25-,26+,27-,28-,29+/m1/s1

Standard InChI Key:  WPVGSIBYLZQSIK-ZAFSJQLXSA-N

Molfile:  

 
     RDKit          2D

 42 47  0  0  0  0  0  0  0  0999 V2000
    6.8044  -10.2242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2090  -11.0696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1788  -12.7093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7462  -13.5001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0719  -11.4412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7897  -11.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4919  -11.4621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4765  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7595  -12.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0573  -12.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3416  -12.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0868  -10.6215    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5157   -8.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5157   -9.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2210  -10.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2210   -8.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9304   -8.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9269   -9.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6331  -10.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3472   -9.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6400   -8.5812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3469   -9.0017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3636   -7.3628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6453   -7.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0704   -7.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0616   -8.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369   -8.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3225   -8.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8512   -7.5362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3387   -8.1802    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0568   -9.4183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0651   -6.9544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8451   -6.7109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5100   -6.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2463   -5.4359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4210   -5.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1731   -6.2290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9357   -4.7804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9231   -8.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6330   -9.4018    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9189  -10.6317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2118   -7.7696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
  6  1  1  0
  7  2  1  6
  8  3  1  6
  9  4  1  6
  6 12  1  6
 13 14  1  0
 13 16  1  0
 14 15  1  0
 15 18  1  0
 17 16  1  0
 17 18  1  0
 17 21  1  0
 18 19  1  0
 19 20  1  0
 20 22  1  0
 21 22  1  0
 21 24  1  0
 22 26  1  0
 25 23  1  0
 23 24  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 25  1  0
 22 30  1  1
 26 31  1  1
 25 32  1  1
 29 33  1  1
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 33  2  0
 36 38  2  0
 17 39  1  1
 21 40  1  6
 18 41  1  6
 14  1  1  1
 39 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4781168

   ---

Molecule Features

Natural Product: Yes

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: 536.66

Molecular Weight (Monoisotopic): 536.2985

AlogP: 1.43

#Rotatable Bonds: 4

Polar Surface Area: 145.91

Molecular Species: NEUTRAL

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.18

CX Basic pKa: 0.24

CX LogP: 1.06

CX LogD: 0.64

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.27

Np Likeness Score: 3.20

References

1. Pederson PJ,Cai S,Carver C,Powell DR,Risinger AL,Grkovic T,O'Keefe BR,Mooberry SL,Cichewicz RH.  (2020)  Triple-Negative Breast Cancer Cells Exhibit Differential Sensitivity to Cardenolides from Calotropis gigantea.,  83  (7.0): [PMID:32649211] [10.1021/acs.jnatprod.0c00423]

Source

Source(1):

• Scientific Literature