SCS-C006517
brefeldin A
Pathway: Polyketides
Superclass: Macrolides
Class: Macrolide lactones
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 sp.
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
DOI:
10.3390/md20070432
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
280.4 Da
Threshold ≤ 500
ALogP
1.96
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C16H24O4
Molecular Weight:
280.3640 Da
SMILES:
C[C@H]1CCC/C=C/[C@@H]2C[C@H](O)C[C@H]2[C@H](O)/C=C/C(=O)O1
InChIKey:
KQNZDYYTLMIZCT-KQPMLPITSA-N
InChI:
InChI=1S/C16H24O4/c1-11-5-3-2-4-6-12-9-13(17)10-14(12)15(18)7-8-16(19)20-11/h4,6-8,11-15,17-18H,2-3,5,9-10H2,1H3/b6-4+,8-7+/t11-,12+,13-,14+,15+/m0/s1
Calculated Properties
ALogP:
1.962 lipophilicity
TPSA:
66.76 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
4
Rotatable Bonds:
0
Ring Count:
2
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.6875 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006517
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Macrolides
NPClassifier Class:
Macrolide lactones
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 | IC50 | Human lung cancer cells | 101.2 nM | 10.3390/md20070432 Marine Drugs |
| Antitumor | IC50 | Human cervical carcinoma cells | 171.9 nM | 10.3390/md20070432 Marine Drugs |
| Antitumor | IC50 | Human hepatoma cells | 239.1 nM | 10.3390/md20070432 Marine Drugs |