SCS-C006227
talaroterpene D
Pathway: Terpenoids
Superclass: Sesquiterpenoids
Class: Eremophilane sesquiterpenoids
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
Talaromyces sp. SCSIO 41412
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Trichocomaceae
Genus
Talaromyces
Species
NA
South China Sea
DOI:
10.3390/md22090403
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
234.3 Da
Threshold ≤ 500
ALogP
2.68
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C15H22O2
Molecular Weight:
234.3390 Da
SMILES:
C=C1COC2C=C3CC[C@@H](O)[C@H](C)[C@@]3(C)CC12
InChIKey:
FOOLKWHUWLVGIN-SXHXBCDNSA-N
InChI:
InChI=1S/C15H22O2/c1-9-8-17-14-6-11-4-5-13(16)10(2)15(11,3)7-12(9)14/h6,10,12-14,16H,1,4-5,7-8H2,2-3H3/t10-,12?,13+,14?,15+/m0/s1
Calculated Properties
ALogP:
2.685 lipophilicity
TPSA:
29.46 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
2
Rotatable Bonds:
0
Ring Count:
3
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.7333 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006227
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesquiterpenoids
NPClassifier Class:
Eremophilane sesquiterpenoids
Glycoside:
No
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 | — | HepG2 cells | Compounds 2 and 4 are non-toxic to cells at concentrations of 200 μM and below. | 10.3390/md22090403 Marine Drugs |
| Metabolic / Lipid regulation | activation/expression regulation | LXRα, ABCA1 | talaroterpene D (4), with a non-toxic concentration of 200 μM, notably stimulated LXRα and its downstream target gene ABCA1 | 10.3390/md22090403 Marine Drugs |
| Other specified activity | expression suppression | FXR, CYP7A1 | significantly suppressed the expression of FXR and downstream CYP7A1. | 10.3390/md22090403 Marine Drugs |
| Metabolic / Lipid regulation | activation/expression regulation | 200 μM | Compounds 1, 3 and 4 (200 μM) exhibited varying degrees of activation on PPARα. Talaroterpene D (4) also showed activation on downstream target genes CPT1α and ACOX1. | 10.3390/md22090403 Marine Drugs |
| Other specified activity | expression regulation | RORα, CLOCK, BMAL1 | it induced significant alterations in the expression of downstream target genes CLOCK and BMAL1 of RORα ... in silico molecular docking analysis supported the direct binding interactions of 4 with RORα protein | 10.3390/md22090403 Marine Drugs |