SCS-C007188
cyclopiazonic acid
Pathway: Alkaloids | Amino acids and Peptides
Superclass: Tetramate alkaloids
Class: Cyclopiazonic acid-tpye tetramate 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
Aspergillus flavus
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus flavus
Dongsha Atoll
· 1781 m
· 117.062°E, 20.077°N
DOI:
10.1016/j.fitote.2021.104839
· Fitoterapia
Drug-likeness (Lipinski Ro5)
Molecular Weight
336.4 Da
Threshold ≤ 500
ALogP
2.83
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C20H20N2O3
Molecular Weight:
336.3910 Da
SMILES:
C/C(O)=C1\C(=O)[C@@H]2[C@H]3c4c[nH]c5cccc(c45)C[C@H]3C(C)(C)N2C1=O
InChIKey:
CNZIQHGDUXRUJS-PTNHGACKSA-N
InChI:
InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,23H,7H2,1-3H3/b14-9-/t12-,16+,17+/m1/s1
Calculated Properties
ALogP:
2.828 lipophilicity
TPSA:
73.40 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
0
Ring Count:
5
(2 aromatic)
Chiral Centers:
3
Fsp³:
0.4000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007188
NPClassifier Pathway:
Alkaloids
Amino acids and Peptides
NPClassifier Superclass:
Tetramate alkaloids
NPClassifier Class:
Cyclopiazonic acid-tpye tetramate 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 |
|---|---|---|---|---|
| Antioxidant | IC50 | DPPH | 62.23 μM | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antitumor | IC50 | SF-268 tumor cells | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antitumor | IC50 | HepG-2 tumor cells | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antitumor | IC50 | MCF-7 tumor cells | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antitumor | IC50 | A549 tumor cells | — Structured numeric value is not available in this record; see the primary reference. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antibacterial | — | Escherichia coli | compounds 4–9 exhibited weak antimicrobial activities against E. coli | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antibacterial | — | Bacillus thuringiensis | compound 9 also showed antibacterial activity against Bacillus thuringiensis, Micrococcus lutea, Staphylococcus aureus, Bacillus subtilis, Methicillin resistant Staphylococcus aureus. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antibacterial | — | Micrococcus lutea | compound 9 also showed antibacterial activity against Bacillus thuringiensis, Micrococcus lutea, Staphylococcus aureus, Bacillus subtilis, Methicillin resistant Staphylococcus aureus. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antibacterial | — | Staphylococcus aureus | compound 9 also showed antibacterial activity against Bacillus thuringiensis, Micrococcus lutea, Staphylococcus aureus, Bacillus subtilis, Methicillin resistant Staphylococcus aureus. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antibacterial | — | Bacillus subtilis | compound 9 also showed antibacterial activity against Bacillus thuringiensis, Micrococcus lutea, Staphylococcus aureus, Bacillus subtilis, Methicillin resistant Staphylococcus aureus. | 10.1016/j.fitote.2021.104839 Fitoterapia |
| Antibacterial | — | Methicillin resistant Staphylococcus aureus | compound 9 also showed antibacterial activity against Bacillus thuringiensis, Micrococcus lutea, Staphylococcus aureus, Bacillus subtilis, Methicillin resistant Staphylococcus aureus. | 10.1016/j.fitote.2021.104839 Fitoterapia |