SCS-C007504

pentactaside C

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

Chemical Structure

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Source Information

Pentacta quadrangularis (sea cucumber)

Kingdom Metazoa Phylum Echinodermata Class Holothuroidea Order Dendrochirotida Family Cucumariidae Genus Colochirus Species Colochirus quadrangularis

South China Sea

DOI: 10.1002/cbdv.200800324 · Chemistry & Biodiversity

Drug-likeness (Lipinski Ro5)

Molecular Weight

1303.4 Da

Threshold ≤ 500

ALogP

-6.23

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:

C55H84Na2O28S2

Molecular Weight:

1303.3630 Da

SMILES:

C=C(C)CCC[C@]1(C)OC(=O)[C@]23CC[C@@H]4C(=CC[C@H]5C(C)(C)[C@@H](O[C@@H]6OC[C@@H](OS(=O)(=O)[O-])C(O)C6O[C@@H]6OC(C)[C@@H](O[C@@H]7OC[C@@H](O)C(O[C@@H]8OC(CO)[C@@H](O)C(OC)C8O)C7O)C(O)C6OS(=O)(=O)[O-])CC[C@]45C)[C@]2(C)C[C@H](OC(C)=O)[C@@H]31.[Na+].[Na+]

InChIKey:

                        RITQJSVSGWGDIB-PBTVESTBSA-L
                        
                    

InChI:

InChI=1S/C55H86O28S2.2Na/c1-24(2)12-11-17-54(9)45-30(75-26(4)57)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)81-54)77-48-43(36(60)32(23-73-48)82-84(65,66)67)80-49-44(83-85(68,69)70)37(61)40(25(3)74-49)78-46-38(62)41(29(58)22-72-46)79-47-39(63)42(71-10)35(59)31(21-56)76-47;;/h13,25,27,29-49,56,58-63H,1,11-12,14-23H2,2-10H3,(H,65,66,67)(H,68,69,70);;/q;2*+1/p-2/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:

-6.230 lipophilicity

TPSA:

410.14 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-C007504

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	IC50	A-549 human lung cancer cells	0.58 μM	10.1002/cbdv.200800324 Chemistry & Biodiversity
Antitumor	IC50	P-388 leukemic cells	1.02 μM	10.1002/cbdv.200800324 Chemistry & Biodiversity
Antitumor	IC50	HCT-116 human colon cancer cells	1.14 μM	10.1002/cbdv.200800324 Chemistry & Biodiversity
Antitumor	IC50	MCF-7 human breast cancer cells	2.3 μM	10.1002/cbdv.200800324 Chemistry & Biodiversity
Antitumor	IC50	MKN-28 human gastric cancer cells	1.12 μM	10.1002/cbdv.200800324 Chemistry & Biodiversity

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