SCS-C008044

intercedenside B

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

Chemical Structure

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Download: SDF SMILES

Source Information

Mensamaria intercedens (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

1259.4 Da

Threshold ≤ 500

ALogP

0.45

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:

C55H86O28S2

Molecular Weight:

1259.3990 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)(CCC=C(C)C)[C@H]8[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]3C)OC[C@H]2O)O[C@H](COS(=O)(=O)O)[C@H]1O

InChIKey:

                        BTKQPLUOMJSJAV-JHQKKJRDSA-N
                        
                    

InChI:

InChI=1S/C55H86O28S2/c1-24(2)12-11-17-54(9)45-30(76-26(4)56)20-53(8)28-13-14-33-51(5,6)34(16-18-52(33,7)27(28)15-19-55(45,53)50(64)82-54)78-49-44(36(59)32(22-73-49)83-85(68,69)70)81-47-38(61)37(60)41(25(3)75-47)79-46-39(62)42(29(57)21-72-46)80-48-40(63)43(71-10)35(58)31(77-48)23-74-84(65,66)67/h12-13,25,27,29-49,57-63H,11,14-23H2,1-10H3,(H,65,66,67)(H,68,69,70)/t25-,27-,29-,30+,31-,32-,33+,34+,35-,36+,37+,38-,39-,40-,41-,42+,43+,44-,45-,46+,47+,48+,49+,52-,53+,54+,55-/m1/s1

Calculated Properties

ALogP:

0.447 lipophilicity

TPSA:

404.48 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (0 aromatic)

Chiral Centers:

Fsp³:

0.8909 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008044

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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