SCS-C007496
arguside 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
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.200790234
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
1175.3 Da
Threshold ≤ 500
ALogP
-1.51
Threshold ≤ 5
H-Bond Donors
12
Threshold ≤ 5
H-Bond Acceptors
25
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C57H90O25
Molecular Weight:
1175.3220 Da
SMILES:
COC1C(O)C(OC2C(O)C(CO)OC(OC3C(C)OC(OC4C(O[C@H]5CC[C@]6(C)C7=C[C@H](O)C89C(=O)O[C@@](C)(CCC=C(C)C)[C@H]8[C@@H](OC(C)=O)C[C@@]9(C)C7CCC6C5(C)C)OCC(O)C4O)C(O)C3O)C2O)OC(CO)C(O)C1O
InChIKey:
SOPBQOGELNCNOP-JQJMHWJSSA-N
InChI:
InChI=1S/C57H90O25/c1-23(2)12-11-16-56(9)47-29(75-25(4)60)19-55(8)26-13-14-32-53(5,6)34(15-17-54(32,7)27(26)18-33(62)57(47,55)52(71)82-56)78-51-46(35(63)28(61)22-73-51)81-48-40(68)39(67)43(24(3)74-48)79-50-42(70)45(37(65)31(21-59)77-50)80-49-41(69)44(72-10)38(66)36(64)30(20-58)76-49/h12,18,24,26,28-51,58-59,61-70H,11,13-17,19-22H2,1-10H3/t24?,26?,28?,29-,30?,31?,32?,33-,34-,35?,36?,37?,38?,39?,40?,41?,42?,43?,44?,45?,46?,47+,48?,49?,50?,51?,54+,55-,56-,57?/m0/s1
Calculated Properties
ALogP:
-1.515 lipophilicity
TPSA:
378.43 Ų polar surface area
H-Bond Donors:
12
H-Bond Acceptors:
25
Rotatable Bonds:
15
Ring Count:
9
(0 aromatic)
Chiral Centers:
30
Fsp³:
0.8947 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007496
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 | HCT-116 human colon cancer cells | 0.14 μM | 10.1002/cbdv.200790234 Chemistry & Biodiversity |
| Antitumor | IC50 | HL-60, BEL-7402, MKN-45 human tumor cell lines | 4.42 μM | 10.1002/cbdv.200790234 Chemistry & Biodiversity |
| Plant / Agricultural | MMDC | Pyricularia oryzae mycelia | 4.0 μg/ml | 10.1002/cbdv.200790234 Chemistry & Biodiversity |