SCS-C007499
25-acetoxy-3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-β-D-xylopyranosyl]-22-oxoholost-9(11)-ene-3β,12α-diol (arguside D)
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Lanostane, Tirucallane and Euphane triterpenoids
Glycoside
Chemical Structure
![Structure of 25-acetoxy-3-O-[3-O-methyl-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→4)-β-D-glucopyranosyl-(1→2)-β-D-xylopyranosyl]-22-oxoholost-9(11)-ene-3β,12α-diol (arguside D)](/scsmarinenp/static/images/structures/SCS-C007499.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
1177.3 Da
Threshold ≤ 500
ALogP
-2.50
Threshold ≤ 5
H-Bond Donors
12
Threshold ≤ 5
H-Bond Acceptors
26
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C56H88O26
Molecular Weight:
1177.2940 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(=O)CCC(C)(C)OC(C)=O)[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:
LUOVUDBTXOVKBZ-KQHHSNFWSA-N
InChI:
InChI=1S/C56H88O26/c1-23(60)81-51(2,3)15-13-32(62)55(8)31-12-17-54(7)24-10-11-30-52(4,5)34(14-16-53(30,6)25(24)18-33(63)56(31,54)50(71)82-55)77-49-45(35(64)26(61)22-73-49)80-46-39(68)38(67)42(29(21-59)76-46)78-48-41(70)44(37(66)28(20-58)75-48)79-47-40(69)43(72-9)36(65)27(19-57)74-47/h18,24,26-31,33-49,57-59,61,63-70H,10-17,19-22H2,1-9H3/t24-,26-,27-,28-,29-,30+,31-,33+,34+,35+,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46+,47+,48+,49+,53-,54+,55-,56+/m1/s1
Calculated Properties
ALogP:
-2.500 lipophilicity
TPSA:
395.50 Ų polar surface area
H-Bond Donors:
12
H-Bond Acceptors:
26
Rotatable Bonds:
17
Ring Count:
9
(0 aromatic)
Chiral Centers:
28
Fsp³:
0.9107 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007499
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 |