SCS-C007359
stichoposide A
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Lanostane, Tirucallane and Euphane triterpenoids
Glycoside
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Thelenota ananas
(NA)
Kingdom
Metazoa
Phylum
Echinodermata
Class
Holothuroidea
Order
Aspidochirotida
Family
Stichopodidae
Genus
Thelenota
Species
Thelenota ananas
South China Sea
DOI:
10.1002/cbdv.202000221
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
793.0 Da
Threshold ≤ 500
ALogP
3.93
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
13
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C43H68O13
Molecular Weight:
793.0040 Da
SMILES:
CC(=O)O[C@@H](CC(C)C)C[C@]1(C)OC(=O)[C@]23CC[C@@H]4C(=CCC5C(C)(C)[C@@H](O[C@@H]6OC[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](C)[C@@H](O)[C@H](O)[C@H]6O)CC[C@@]54C)[C@]2(C)CC[C@@H]31
InChIKey:
FRVKPMUWTMTMIA-OMAOWMMESA-N
InChI:
InChI=1S/C43H68O13/c1-21(2)18-24(53-23(4)44)19-42(9)29-13-16-41(8)26-10-11-28-39(5,6)30(14-15-40(28,7)25(26)12-17-43(29,41)38(50)56-42)54-37-35(32(47)27(45)20-51-37)55-36-34(49)33(48)31(46)22(3)52-36/h10,21-22,24-25,27-37,45-49H,11-20H2,1-9H3/t22-,24+,25-,27-,28?,29-,30+,31-,32+,33+,34-,35-,36+,37+,40-,41+,42+,43-/m1/s1
Calculated Properties
ALogP:
3.931 lipophilicity
TPSA:
190.67 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
13
Rotatable Bonds:
9
Ring Count:
7
(0 aromatic)
Chiral Centers:
18
Fsp³:
0.9070 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007359
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Lanostane, Tirucallane and Euphane triterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
Activity values are displayed only when a quantitative or clearly reported result is available.
Tested organisms, cell lines and molecular targets are shown under Target / model.
| Activity | Assay | Target / model | Result | Reference |
|---|---|---|---|---|
| Antitumor | preliminary activity screen | Cancer cells | After preliminary activity detection (Supplementary Materials, Figure S1, Table S3), we decided to select STC2 with strong antitumour activity and low cytotoxicity to normal cells for subsequent pharmacological studies. | 10.1002/cbdv.202000221 Chemistry & Biodiversity |