SCS-C007500
3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-β-D-xylopyranosyl]-22,25-epoxyholost-9(11)-ene-3β,12α-diol (arguside E)
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Lanostane, Tirucallane and Euphane triterpenoids
Glycoside
Chemical Structure
![Structure of 3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-β-D-xylopyranosyl]-22,25-epoxyholost-9(11)-ene-3β,12α-diol (arguside E)](/scsmarinenp/static/images/structures/SCS-C007500.png)
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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
Bohadschia argus
(sea cucumber)
Original source name: Bohadschia argus Jaeger
Kingdom
Metazoa
Phylum
Echinodermata
Class
Holothuroidea
Order
Aspidochirotida
Family
Holothuriidae
Genus
Bohadschia
Species
Bohadschia argus
South China Sea
· 3-30 m
DOI:
10.1002/cbdv.200890115
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
1119.3 Da
Threshold ≤ 500
ALogP
-2.23
Threshold ≤ 5
H-Bond Donors
12
Threshold ≤ 5
H-Bond Acceptors
24
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C54H86O24
Molecular Weight:
1119.2580 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)C7=C[C@H](O)[C@]89C(=O)O[C@@](C)([C@@H]%10CCC(C)(C)O%10)[C@H]8CC[C@@]9(C)[C@@H]7CC[C@H]6C5(C)C)OC[C@H](O)[C@@H]4O)O[C@@H]3CO)O[C@H](CO)[C@H]2O)O[C@H](CO)[C@H]1O
InChIKey:
IGGIDIDIRQTJRC-RNBXQOTRSA-N
InChI:
InChI=1S/C54H86O24/c1-49(2)14-12-32(77-49)53(7)29-11-16-52(6)22-9-10-28-50(3,4)31(13-15-51(28,5)23(22)17-30(59)54(29,52)48(67)78-53)73-47-43(33(60)24(58)21-69-47)76-44-37(64)36(63)40(27(20-57)72-44)74-46-39(66)42(35(62)26(19-56)71-46)75-45-38(65)41(68-8)34(61)25(18-55)70-45/h17,22,24-47,55-66H,9-16,18-21H2,1-8H3/t22-,24+,25-,26-,27-,28+,29-,30+,31+,32+,33+,34-,35-,36+,37-,38-,39-,40+,41+,42+,43-,44+,45+,46+,47+,51-,52+,53-,54+/m1/s1
Calculated Properties
ALogP:
-2.233 lipophilicity
TPSA:
361.36 Ų polar surface area
H-Bond Donors:
12
H-Bond Acceptors:
24
Rotatable Bonds:
13
Ring Count:
10
(0 aromatic)
Chiral Centers:
29
Fsp³:
0.9444 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007500
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 |
|---|---|---|---|---|
| Antitumor | IC50 | human lung cancer A-549 cells | 3.36–7.77 μg/ml | 10.1002/cbdv.200890115 Chemistry & Biodiversity |
| Antitumor | IC50 | human colon cancer HCT-116 cells | 3.36–7.77 μg/ml | 10.1002/cbdv.200890115 Chemistry & Biodiversity |
| Antitumor | IC50 | human hepatoma HepG2 cells | 3.36–7.77 μg/ml | 10.1002/cbdv.200890115 Chemistry & Biodiversity |
| Antitumor | IC50 | human breast cancer MCF-7 cells | 3.36–7.77 μg/ml | 10.1002/cbdv.200890115 Chemistry & Biodiversity |