SCS-C005986

variegatuside D

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

Chemical Structure

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Source Information

Stichopus variegates Semper (sea cucumber)

Kingdom Metazoa Phylum Echinodermata Class Holothuroidea Order Aspidochirotida Family Stichopodidae Genus Stichopus Species Stichopus horrens

South China Sea

DOI: 10.3390/md12042004 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

1237.4 Da

Threshold ≤ 500

ALogP

-2.76

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:

C59H96O27

Molecular Weight:

1237.3900 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]4[C@H](O[C@H]5CC[C@]6(C)C7=C(CC[C@H]6C5(C)C)[C@]5(C)CC[C@H]6[C@]5(CC7)C(=O)O[C@@]6(C)C[C@H](O)CC(C)C)OC[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H]4O)O[C@H](CO)[C@H]3O)OC[C@H]2O)O[C@H](CO)[C@H]1O

InChIKey:

                        JQYSCLHUKFMTBZ-MXLVDXNBSA-N
                        
                    

InChI:

InChI=1S/C59H96O27/c1-24(2)17-25(63)18-58(7)34-12-15-57(6)27-9-10-33-55(3,4)35(13-14-56(33,5)26(27)11-16-59(34,57)54(74)86-58)82-53-48(39(68)32(23-77-53)81-50-41(70)40(69)36(65)29(19-60)78-50)85-52-44(73)47(38(67)31(21-62)80-52)84-49-42(71)45(28(64)22-76-49)83-51-43(72)46(75-8)37(66)30(20-61)79-51/h24-25,28-53,60-73H,9-23H2,1-8H3/t25-,28-,29-,30-,31-,32-,33+,34-,35+,36-,37-,38-,39+,40+,41-,42-,43-,44-,45+,46+,47+,48-,49+,50+,51+,52+,53+,56-,57+,58+,59-/m1/s1

Calculated Properties

ALogP:

-2.757 lipophilicity

TPSA:

411.05 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

10 (0 aromatic)

Chiral Centers:

Fsp³:

0.9492 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005986

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
Antifungal	MC80	in vitro assay against six fungal strains	— Structured numeric value is not available in this record; see the primary reference.	10.3390/md12042004 Marine Drugs

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