SCS-C005989
variegatuside A
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Lanostane, Tirucallane and Euphane triterpenoids
Glycoside
Chemical Structure
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
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
1075.2 Da
Threshold ≤ 500
ALogP
-0.73
Threshold ≤ 5
H-Bond Donors
11
Threshold ≤ 5
H-Bond Acceptors
22
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C53H86O22
Molecular Weight:
1075.2490 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](CO)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@@H](O)CC(C)C)[C@H]8CC[C@@]9(C)C7=CC[C@H]6C5(C)C)OC[C@@H](O)[C@@H]4O)[C@@H]3O)OC[C@H]2O)O[C@H](CO)[C@H]1O
InChIKey:
KZTNTKKMZRHISO-JOUVSOKHSA-N
InChI:
InChI=1S/C53H86O22/c1-23(2)17-24(56)18-52(7)32-12-15-51(6)26-9-10-31-49(3,4)33(13-14-50(31,5)25(26)11-16-53(32,51)48(65)75-52)71-47-43(34(59)27(57)21-68-47)74-46-39(64)42(36(61)30(20-55)70-46)73-44-37(62)40(28(58)22-67-44)72-45-38(63)41(66-8)35(60)29(19-54)69-45/h9,23-25,27-47,54-64H,10-22H2,1-8H3/t24-,25+,27+,28+,29+,30+,31-,32+,33-,34-,35+,36-,37+,38+,39+,40-,41-,42-,43+,44-,45-,46-,47-,50-,51-,52-,53+/m0/s1
Calculated Properties
ALogP:
-0.726 lipophilicity
TPSA:
331.90 Ų polar surface area
H-Bond Donors:
11
H-Bond Acceptors:
22
Rotatable Bonds:
15
Ring Count:
9
(0 aromatic)
Chiral Centers:
27
Fsp³:
0.9434 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005989
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Lanostane, Tirucallane and Euphane triterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 |