SCS-C007356
stichloroside C2
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Lanostane, Tirucallane and Euphane triterpenoids
Glycoside
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Thelenota ananas
(NA)
Kingdom
Metazoa
Phylum
Echinodermata
Class
Holothuroidea
Order
Aspidochirotida
Family
Stichopodidae
Genus
Thelenota
Species
Thelenota ananas
South China Sea
DOI:
10.1002/cbdv.202000221
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
1437.6 Da
Threshold ≤ 500
ALogP
-2.90
Threshold ≤ 5
H-Bond Donors
14
Threshold ≤ 5
H-Bond Acceptors
32
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C68H108O32
Molecular Weight:
1437.5800 Da
SMILES:
C=C(C)CC(CC1(C)OC(=O)C23CCC4C(=CCC5C(C)(C)C(OC6OC(CO)C(O)C(OC7OC(CO)C(O)C(OC)C7O)C6OC6OC(C)C(OC7OCC(OC8OCC(O)C(OC9OC(CO)C(O)C(OC)C9O)C8O)C(O)C7O)C(O)C6O)CCC45C)C2(C)CCC13)OC(C)=O
InChIKey:
XUSLYKOYHLINDU-UHFFFAOYSA-N
InChI:
InChI=1S/C68H108O32/c1-27(2)20-30(90-29(4)72)21-67(9)39-15-18-66(8)32-12-13-38-64(5,6)40(16-17-65(38,7)31(32)14-19-68(39,66)63(84)100-67)95-62-56(55(44(77)36(24-71)93-62)98-61-50(83)54(86-11)43(76)35(23-70)92-61)99-59-47(80)45(78)51(28(3)89-59)96-57-46(79)41(74)37(26-88-57)94-58-48(81)52(33(73)25-87-58)97-60-49(82)53(85-10)42(75)34(22-69)91-60/h12,28,30-31,33-62,69-71,73-83H,1,13-26H2,2-11H3
Calculated Properties
ALogP:
-2.905 lipophilicity
TPSA:
465.04 Ų polar surface area
H-Bond Donors:
14
H-Bond Acceptors:
32
Rotatable Bonds:
22
Ring Count:
11
(0 aromatic)
Chiral Centers:
37
Fsp³:
0.9118 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007356
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 | MCF-7, MDA-MB-231, 4T1 breast cancer cells | < 5.0 μM | 10.1002/cbdv.202000221 Chemistry & Biodiversity |
| Antitumor | inhibition rate | MDA-MB-231, 4T1 TNBC cells | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.202000221 Chemistry & Biodiversity |
| Antitumor | cell cycle arrest | MDA-MB-231 | cell cycle of MDA-MB-231 cells treated with STC2 was arrested in the G2/M phase; cycle of 4T1 cells treated with STC2 was blocked in the S phase | 10.1002/cbdv.202000221 Chemistry & Biodiversity |
| Antitumor | protein expression upregulation | γ-H2AX (DNA double-strand break marker) | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.202000221 Chemistry & Biodiversity |
| Antitumor | apoptosis induction | MDA-MB-231 | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.202000221 Chemistry & Biodiversity |
| Other specified activity | protein expression regulation | E-cadherin, vimentin | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.202000221 Chemistry & Biodiversity |
| Receptor / Signaling modulation | protein phosphorylation regulation | Akt | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.202000221 Chemistry & Biodiversity |