SCS-C007497
arguside B
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.200890115
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
1443.6 Da
Threshold ≤ 500
ALogP
-4.92
Threshold ≤ 5
H-Bond Donors
17
Threshold ≤ 5
H-Bond Acceptors
33
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C67H110O33
Molecular Weight:
1443.5840 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)(CCCC(C)C)[C@@]8(O)CC[C@@]9(C)[C@@H]7CC[C@@H]6C5(C)C)OC[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](OC)[C@H]6O)[C@H]5O)[C@@H]4O)O[C@@H]3C)O[C@H](CO)[C@H]2O)O[C@H](CO)[C@H]1O
InChIKey:
ZWKMMHZRZDMZLT-UJVHJQPWSA-N
InChI:
InChI=1S/C67H110O33/c1-26(2)12-11-16-65(8)66(85)19-18-64(7)28-13-14-35-62(4,5)37(15-17-63(35,6)29(28)20-36(72)67(64,66)61(84)100-65)95-60-54(42(77)34(25-88-60)94-56-47(82)52(40(75)32(23-70)90-56)97-57-45(80)50(86-9)38(73)30(21-68)91-57)99-55-44(79)43(78)49(27(3)89-55)96-59-48(83)53(41(76)33(24-71)93-59)98-58-46(81)51(87-10)39(74)31(22-69)92-58/h20,26-28,30-60,68-83,85H,11-19,21-25H2,1-10H3/t27-,28-,30-,31-,32-,33-,34+,35-,36+,37+,38-,39-,40-,41-,42+,43-,44-,45-,46-,47-,48-,49-,50+,51+,52+,53+,54-,55+,56+,57+,58+,59+,60+,63-,64+,65+,66+,67-/m1/s1
Calculated Properties
ALogP:
-4.920 lipophilicity
TPSA:
499.43 Ų polar surface area
H-Bond Donors:
17
H-Bond Acceptors:
33
Rotatable Bonds:
22
Ring Count:
11
(0 aromatic)
Chiral Centers:
38
Fsp³:
0.9552 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007497
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 | A549 | 0.48 μg/ml | 10.1002/cbdv.200890115 Chemistry & Biodiversity |
| Antitumor | IC50 | HCT-116 | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.200890115 Chemistry & Biodiversity |
| Antitumor | IC50 | HepG2 | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.200890115 Chemistry & Biodiversity |
| Antitumor | IC50 | MCF-7 | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.200890115 Chemistry & Biodiversity |