SCS-C008045

intercedenside C

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

Chemical Structure

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Source Information

Mensamaria intercedens Lampert (sea cucumber)

Original source name: Mensamria intercedens Lampert

Kingdom Metazoa Phylum Echinodermata Class Holothuroidea Order Dendrochirotida Family Cucumariidae Genus Mensamaria Species Mensamaria intercedens

South China Sea · 3-30 m

DOI: 10.1021/np030064y · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

1209.3 Da

Threshold ≤ 500

ALogP

-1.52

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:

C55H84O27S

Molecular Weight:

1209.3170 Da

SMILES:

CO[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@@H]3[C@@H](O)[C@@H](O)[C@H](O[C@H]4[C@H](O[C@H]5CC[C@]6(C)[C@@H]7CC[C@]89C(=O)O[C@@](C)(/C=C/C=C(C)C)[C@@]8(O)[C@@H](OC(C)=O)C[C@@]9(C)C7=CC[C@H]6C5(C)C)OC[C@@H](OS(=O)(=O)O)[C@@H]4O)O[C@@H]3CO)OC[C@H]2O)O[C@H](CO)[C@H]1O

InChIKey:

                        ABUYDFJTKKJHKG-JYXUVRDZSA-N
                        
                    

InChI:

InChI=1S/C55H84O27S/c1-24(2)11-10-16-53(8)55(67)34(74-25(3)58)19-52(7)27-12-13-32-50(4,5)33(15-17-51(32,6)26(27)14-18-54(52,55)49(66)81-53)77-48-44(36(61)31(23-73-48)82-83(68,69)70)80-46-38(63)37(62)42(30(21-57)76-46)79-45-39(64)41(28(59)22-72-45)78-47-40(65)43(71-9)35(60)29(20-56)75-47/h10-12,16,26,28-48,56-57,59-65,67H,13-15,17-23H2,1-9H3,(H,68,69,70)/b16-10+/t26-,28-,29-,30-,31-,32+,33+,34+,35-,36+,37+,38-,39-,40-,41+,42+,43+,44-,45+,46+,47+,48+,51-,52+,53+,54-,55+/m1/s1

Calculated Properties

ALogP:

-1.517 lipophilicity

TPSA:

401.57 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (0 aromatic)

Chiral Centers:

Fsp³:

0.8545 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008045

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	ED50	10 human tumor cell lines (A549, MCF-7, IA9, CAKI-1, U-87-MG, PC-3, KB, KB-VIN, SK-MEL-2, HCT-8)	0.6–4.0 μg/mL	10.1021/np030064y Journal of Natural Products

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