SCS-C007092
pestalotiochromone A
Pathway: Terpenoids
Superclass: Meroterpenoids
Class: Tetraketide meroterpenoids
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
(SCSIO41403)
Kingdom
Fungi
Phylum
Ascomycota
Class
Sordariomycetes
Order
Amphisphaeriales
Family
Sporocadaceae
Genus
Pestalotiopsis
Species
Pestalotiopsis neglecta
South China Sea
DOI:
10.1016/j.bioorg.2021.104927
· Bioorganic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
360.4 Da
Threshold ≤ 500
ALogP
5.00
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C21H28O5
Molecular Weight:
360.4500 Da
SMILES:
CC(C)=CCC/C(C)=C/CC[C@@]1(C)CC(=O)c2cc(O)c(O)c(O)c2O1
InChIKey:
SCXMONWTTYXKCY-PBAKHKOTSA-N
InChI:
InChI=1S/C21H28O5/c1-13(2)7-5-8-14(3)9-6-10-21(4)12-17(23)15-11-16(22)18(24)19(25)20(15)26-21/h7,9,11,22,24-25H,5-6,8,10,12H2,1-4H3/b14-9+/t21-/m0/s1
Calculated Properties
ALogP:
5.000 lipophilicity
TPSA:
86.99 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
5
Rotatable Bonds:
6
Ring Count:
2
(1 aromatic)
Chiral Centers:
1
Fsp³:
0.4762 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007092
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Tetraketide meroterpenoids
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 | inhibitory | ACHN, OS-RC-2, 786-O, HL-60, K-562, MOLT-4, HepG2 cancer cell lines | > 50.0 μM | 10.1016/j.bioorg.2021.104927 Bioorganic Chemistry |
| Metabolic / Lipid regulation | agonistic | LXRα | 6.2 μM | 10.1016/j.bioorg.2021.104927 Bioorganic Chemistry |
| Receptor / Signaling modulation | upregulatory | LXRβ, ABCA1 | the downstream gene ABCA1 and LXRβ were significantly upregulated by 3, 5, and 6 | 10.1016/j.bioorg.2021.104927 Bioorganic Chemistry |