SCS-C006844
(±)-oxypenicinoline A
Pathway: Alkaloids
Superclass: Anthranilic acid alkaloids
Class: Acridone alkaloids
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
Penicillium steckii SCSIO 41025
(Penicillium)
Original source name: Penicillium steckii SCSIO 41025 (Trichocomaceae)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium steckii
South China Sea
· 21.235 N, 110.451 E
DOI:
10.1016/j.phytochem.2021.112730
· Phytochemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
256.3 Da
Threshold ≤ 500
ALogP
0.54
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C14H12N2O3
Molecular Weight:
256.2610 Da
SMILES:
Cn1c2c(c(=O)c3ccccc31)C(=O)N1CCC21O
InChIKey:
ZQGJBEVODUFSSP-UHFFFAOYSA-N
InChI:
InChI=1S/C14H12N2O3/c1-15-9-5-3-2-4-8(9)11(17)10-12(15)14(19)6-7-16(14)13(10)18/h2-5,19H,6-7H2,1H3
Calculated Properties
ALogP:
0.543 lipophilicity
TPSA:
62.54 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
0
Ring Count:
4
(2 aromatic)
Chiral Centers:
1
Fsp³:
0.2857 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006844
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Anthranilic acid alkaloids
NPClassifier Class:
Acridone alkaloids
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 |
|---|---|---|---|---|
| Enzyme inhibition | IC50 | α-glucosidase (from Saccharomyces cerevisiae) | 317.8 μM | 10.1016/j.phytochem.2021.112730 Phytochemistry |
| Enzyme inhibition | IC50 | AChE | compounds 7 and 9 showed moderate inhibitions against AChE with the IC50 values of 87.3 and 68.5 μM; while (±)-2–4 displayed nearly no inhibitions against α-glucosidase, none other reported AChE activity for 1 | 10.1016/j.phytochem.2021.112730 Phytochemistry |