SCS-C007358

stichoposide C1

Pathway: Terpenoids Superclass: Triterpenoids Class: Lanostane, Tirucallane and Euphane triterpenoids Glycoside

Chemical Structure

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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

1439.6 Da

Threshold ≤ 500

ALogP

-2.82

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

3 violations (MW, HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C68H110O32

Molecular Weight:

1439.5960 Da

SMILES:

CO[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@@H]3CO[C@@H](O[C@H]4CC[C@]5(C)[C@@H]6CCC78C(=O)O[C@@](C)(C[C@H](CC(C)C)OC(C)=O)[C@H]7CC[C@@]8(C)C6=CC[C@H]5C4(C)C)[C@H](OC4O[C@H](C)[C@@H](O[C@@H]5OC[C@@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]6O)[C@H]5O)[C@H](O)[C@H]4O)[C@H]3O)O[C@H](CO)[C@H]2O)O[C@H](CO)[C@H]1O

InChIKey:

                        OHVCWYKNFLTBKL-FVKDKELCSA-N
                        
                    

InChI:

InChI=1S/C68H110O32/c1-27(2)20-30(90-29(4)72)21-67(9)39-15-18-66(8)32-12-13-38-64(5,6)40(16-17-65(38,7)31(32)14-19-68(39,66)63(84)100-67)95-62-56(44(77)37(26-88-62)94-59-50(83)55(43(76)36(24-71)91-59)98-61-49(82)54(86-11)42(75)35(23-70)93-61)99-58-46(79)45(78)51(28(3)89-58)96-57-47(80)52(33(73)25-87-57)97-60-48(81)53(85-10)41(74)34(22-69)92-60/h12,27-28,30-31,33-62,69-71,73-83H,13-26H2,1-11H3/t28-,30+,31-,33-,34-,35-,36-,37-,38+,39-,40+,41-,42-,43-,44+,45-,46-,47-,48-,49-,50-,51-,52+,53+,54+,55+,56-,57+,58?,59+,60+,61+,62+,65-,66+,67+,68?/m1/s1

Calculated Properties

ALogP:

-2.825 lipophilicity

TPSA:

465.04 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

11 (0 aromatic)

Chiral Centers:

Fsp³:

0.9412 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007358

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Triterpenoids

NPClassifier Class:

Lanostane, Tirucallane and Euphane triterpenoids

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

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

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