SCS-C008326
N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline
Pathway: Alkaloids
Superclass: Proline alkaloids
Class: Pyrrole 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 citrinum
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium citrinum
South China Sea
DOI:
10.1021/acs.jafc.5c15871
· Journal of Agricultural and Food Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
249.4 Da
Threshold ≤ 500
ALogP
3.07
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
2
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C15H23NO2
Molecular Weight:
249.3540 Da
SMILES:
C/C=C/CCCCC(=O)C(C)C(=O)N1C=CCC1
InChIKey:
JGNMZTXDOHXIJQ-ONEGZZNKSA-N
InChI:
InChI=1S/C15H23NO2/c1-3-4-5-6-7-10-14(17)13(2)15(18)16-11-8-9-12-16/h3-4,8,11,13H,5-7,9-10,12H2,1-2H3/b4-3+
Calculated Properties
ALogP:
3.074 lipophilicity
TPSA:
37.38 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
2
Rotatable Bonds:
7
Ring Count:
1
(0 aromatic)
Chiral Centers:
1
Fsp³:
0.6000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008326
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Proline alkaloids
NPClassifier Class:
Pyrrole 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 |
|---|---|---|---|---|
| Other specified activity | enzyme inhibition | OfChtII and OfChi-h | These compounds were first evaluated for chitinase (OfChtII and OfChi-h) inhibition, revealing that both the 3-pyrroline ring and the Δ8′,9′ double bond are key functional groups. | 10.1021/acs.jafc.5c15871 Journal of Agricultural and Food Chemistry |
| Other specified activity | larval mortality | Plutella xylostella larvae | 100.0 % | 10.1021/acs.jafc.5c15871 Journal of Agricultural and Food Chemistry |
| Antifungal | — | — | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jafc.5c15871 Journal of Agricultural and Food Chemistry |
| Other specified activity | anti-JH activity | Oncopeltus fasciatus fourth-instar nymphs | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.jafc.5c15871 Journal of Agricultural and Food Chemistry |