SCS-C006320
6'-O-(n-butanol) ilekudinoside B ester
Pathway: Terpenoids
Superclass: Triterpenoids
Class: Ursane and Taraxastane 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
Avicennia marina
(mangrove fruit)
Kingdom
Viridiplantae
Phylum
Streptophyta
Class
Magnoliopsida
Order
Lamiales
Family
Acanthaceae
Genus
Avicennia
Species
Avicennia marina
South China Sea
DOI:
10.1007/s13659-018-0167-9
· Natural Products and Bioprospecting
Drug-likeness (Lipinski Ro5)
Molecular Weight
867.1 Da
Threshold ≤ 500
ALogP
2.64
Threshold ≤ 5
H-Bond Donors
8
Threshold ≤ 5
H-Bond Acceptors
15
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C46H74O15
Molecular Weight:
867.0830 Da
SMILES:
CCCCOC(=O)[C@H]1O[C@@H](OC2CC[C@@]3(C)C(CC[C@]4(C)C3CC=C3C5[C@](C(=O)O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)(CC[C@@H](C)[C@@]5(C)O)CC[C@]34C)C2(C)C)[C@H](O)C(O)[C@@H]1O
InChIKey:
XBHKCWGOWPRPGY-LYBUSXANSA-N
InChI:
InChI=1S/C46H74O15/c1-9-10-21-57-37(54)35-32(51)31(50)34(53)39(60-35)59-28-15-16-42(5)26(41(28,3)4)14-17-44(7)27(42)12-11-24-36-45(8,56)23(2)13-18-46(36,20-19-43(24,44)6)40(55)61-38-33(52)30(49)29(48)25(22-47)58-38/h11,23,25-36,38-39,47-53,56H,9-10,12-22H2,1-8H3/t23-,25-,26?,27?,28?,29-,30+,31?,32+,33-,34-,35+,36?,38+,39-,42+,43-,44-,45-,46+/m1/s1
Calculated Properties
ALogP:
2.638 lipophilicity
TPSA:
242.13 Ų polar surface area
H-Bond Donors:
8
H-Bond Acceptors:
15
Rotatable Bonds:
9
Ring Count:
7
(0 aromatic)
Chiral Centers:
20
Fsp³:
0.9130 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006320
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Triterpenoids
NPClassifier Class:
Ursane and Taraxastane 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 glioma stem cells | 12.21 μg/mL | 10.1007/s13659-018-0167-9 Natural Products and Bioprospecting |
| Antitumor | IC50 | human glioma stem cells | 5.53 μg/mL | 10.1007/s13659-018-0167-9 Natural Products and Bioprospecting |