SCS-C007968
pestalotioquinoside C
Pathway: Terpenoids
Superclass: Meroterpenoids
Class: Miscellaneous meroterpenoids
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
Pestalotiopsis neglecta SCSIO 41403
(SCSIO41403)
Original source name: Pestalotiopsis neglecta SCSIO41403
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Amphisphaeriales
Family
Sporocadaceae
Genus
Pestalotiopsis
Species
Pestalotiopsis neglecta
South China Sea
DOI:
10.1021/acs.jnatprod.0c00050
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
388.5 Da
Threshold ≤ 500
ALogP
2.25
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H28O6
Molecular Weight:
388.4600 Da
SMILES:
C=C(C#Cc1cc(O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)ccc1O)CCC=C(C)C
InChIKey:
NRDCSLAQSOIIRI-RMGTVLPZSA-N
InChI:
InChI=1S/C22H28O6/c1-13(2)6-5-7-14(3)8-9-16-12-17(10-11-18(16)23)28-22-21(26)20(25)19(24)15(4)27-22/h6,10-12,15,19-26H,3,5,7H2,1-2,4H3/t15-,19-,20+,21+,22-/m0/s1
Calculated Properties
ALogP:
2.253 lipophilicity
TPSA:
99.38 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
6
Rotatable Bonds:
5
Ring Count:
2
(1 aromatic)
Chiral Centers:
5
Fsp³:
0.4545 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007968
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Miscellaneous meroterpenoids
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 | ACHN, OS-RC-2, 786-O, HL-60, K-562, MOLT-4 cell lines | > 50.0 μM | 10.1021/acs.jnatprod.0c00050 Journal of Natural Products |
| Antiviral | — | Dengue virus | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jnatprod.0c00050 Journal of Natural Products |
| Receptor / Signaling modulation | KD | LXRα receptor | 50.0 μM | 10.1021/acs.jnatprod.0c00050 Journal of Natural Products |
| Metabolic / Lipid regulation | — | ABCA1 gene | a canonical LXR target gene, ABCA1, was significantly upregulated by 8, which revealed 8 as a potential LXRα agonist. | 10.1021/acs.jnatprod.0c00050 Journal of Natural Products |