SCS-C007495
hillaside C
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
Holothuria hilla
(sea cucumber)
Kingdom
Metazoa
Phylum
Echinodermata
Class
Holothuroidea
Order
Aspidochirotida
Family
Holothuriidae
Genus
Holothuria
Species
Holothuria hilla
South China Sea
· 3–30 m
DOI:
10.1002/cbdv.200690126
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
871.0 Da
Threshold ≤ 500
ALogP
-2.31
Threshold ≤ 5
H-Bond Donors
7
Threshold ≤ 5
H-Bond Acceptors
17
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C40H63NaO17S
Molecular Weight:
870.9840 Da
SMILES:
CC(C)(O)CCC[C@]1(C)OC(=O)C23[C@@H](O)C=C4C(CCC5C(C)(C)[C@@H](OC6OCC(OS(=O)(=O)[O-])C(O)C6OC6OCC(O)C(O)C6O)CC[C@]45C)[C@]2(C)CC[C@@]31O.[Na+]
InChIKey:
PXBMGMVPHGJSSY-DUJDNZASSA-M
InChI:
InChI=1S/C40H64O17S.Na/c1-34(2,47)12-8-13-38(7)39(48)16-15-37(6)20-9-10-24-35(3,4)26(11-14-36(24,5)21(20)17-25(42)40(37,39)33(46)56-38)54-32-30(28(44)23(19-53-32)57-58(49,50)51)55-31-29(45)27(43)22(41)18-52-31;/h17,20,22-32,41-45,47-48H,8-16,18-19H2,1-7H3,(H,49,50,51);/q;+1/p-1/t20?,22?,23?,24?,25-,26-,27?,28?,29?,30?,31?,32?,36+,37-,38-,39-,40?;/m0./s1
Calculated Properties
ALogP:
-2.310 lipophilicity
TPSA:
271.26 Ų polar surface area
H-Bond Donors:
7
H-Bond Acceptors:
17
Rotatable Bonds:
10
Ring Count:
7
(0 aromatic)
Chiral Centers:
17
Fsp³:
0.9250 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007495
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 | CAKI-1 cells | 0.15 μg/ml | 10.1002/cbdv.200690126 Chemistry & Biodiversity |
| Antitumor | IC50 | eight human tumor cell lines (A-549, MCF-7, IA9, CAKI-1, PC-3, KB, KB-VIN, HCT-8) | 3.2 μg/ml | 10.1002/cbdv.200690126 Chemistry & Biodiversity |