Calotoxin

ID: ALA4743046

PubChem CID: 101710282

Max Phase: Preclinical

Molecular Formula: C29H40O10

Molecular Weight: 548.63

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H]1O[C@H]2O[C@@H]3C[C@@H]4CC[C@@H]5[C@H](CC[C@]6(C)[C@@H](C7=CC(=O)OC7)CC[C@]56O)[C@@]4(C=O)C[C@H]3O[C@@]2(O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C29H40O10/c1-14-23(32)24(33)29(35)25(37-14)38-20-10-16-3-4-19-18(27(16,13-30)11-21(20)39-29)5-7-26(2)17(6-8-28(19,26)34)15-9-22(31)36-12-15/h9,13-14,16-21,23-25,32-35H,3-8,10-12H2,1-2H3/t14-,16+,17-,18+,19-,20-,21-,23-,24-,25+,26-,27-,28+,29+/m1/s1

Standard InChI Key:  LYSHVSOMKBORDM-NFYSVIEISA-N

Molfile:  

 
     RDKit          2D

 45 51  0  0  0  0  0  0  0  0999 V2000
   17.6723   -9.5628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6723   -7.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3817   -8.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3783   -9.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0844   -9.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7986   -9.1643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0914   -7.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7982   -8.3455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8149   -6.7066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0967   -7.1064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5218   -7.1230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5129   -7.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2883   -8.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7738   -7.5476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3026   -6.8800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7901   -7.5239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5082   -8.7621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5165   -6.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2965   -6.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9614   -5.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6977   -4.7797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8723   -4.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6245   -5.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3870   -4.1241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3744   -7.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0843   -8.7456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.3703   -9.9755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6631   -7.1134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9670   -9.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9670   -8.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2597   -7.9286    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2597   -9.5712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5478   -9.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5484   -8.3370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8413   -7.9281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1291   -8.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1286   -9.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8402   -9.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4223   -7.9259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8430   -7.1109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5431   -9.9755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.5431   -7.5198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9629   -7.5198    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4201   -9.5647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9629   -9.9755    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 30  2  1  0
 29  1  1  0
  1  4  1  0
  3  2  1  0
  3  4  1  0
  3  7  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  7  8  1  0
  7 10  1  0
  8 12  1  0
 11  9  1  0
  9 10  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 11  1  0
  8 16  1  1
 12 17  1  1
 11 18  1  1
 15 19  1  1
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  2  0
 22 24  2  0
  3 25  1  1
  7 26  1  6
  4 27  1  6
 25 28  2  0
 29 30  1  0
 29 32  1  0
 30 31  1  0
 31 34  1  0
 33 32  1  0
 33 34  1  0
 33 38  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 36 39  1  1
 35 40  1  1
 33 41  1  1
 34 42  1  1
 30 43  1  1
 37 44  1  6
 29 45  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4743046

   (1S,3R,5S,7R,8S,9R,10S,12R,14R,15S,18R,19R,22S,23R)-8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde

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: 548.63

Molecular Weight (Monoisotopic): 548.2621

AlogP: 0.97

#Rotatable Bonds: 2

Polar Surface Area: 151.98

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.18

CX Basic pKa: 0.27

CX LogP: 1.27

CX LogD: 0.85

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.22

Np Likeness Score: 3.40

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