SCS-C000383
isochromophilone IX
Pathway: Polyketides
Superclass: Chromanes
Class: Azaphilones
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
Penicillium sclerotiorum CHNSCLM-0013
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium sclerotiorum
South China Sea
DOI:
10.1016/j.bioorg.2019.102973
· Bioorganic Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
476.0 Da
Threshold ≤ 500
ALogP
4.45
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C25H30ClNO6
Molecular Weight:
476.0000 Da
SMILES:
CCC(C)/C=C(C)/C=C/C1=CC2=C(Cl)C(=O)C(C)(OC(C)=O)C(=O)C2=CN1CCCC(=O)O
InChIKey:
SAMXBYLRDCRTCV-HMSDUJDUSA-N
InChI:
InChI=1S/C25H30ClNO6/c1-6-15(2)12-16(3)9-10-18-13-19-20(14-27(18)11-7-8-21(29)30)23(31)25(5,33-17(4)28)24(32)22(19)26/h9-10,12-15H,6-8,11H2,1-5H3,(H,29,30)/b10-9+,16-12+
Calculated Properties
ALogP:
4.450 lipophilicity
TPSA:
100.98 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
6
Rotatable Bonds:
9
Ring Count:
2
(0 aromatic)
Chiral Centers:
2
Fsp³:
0.4400 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000383
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Chromanes
NPClassifier Class:
Azaphilones
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 |
|---|---|---|---|---|
| Anti-inflammatory | IC50 | NO production | 17.6 μM | 10.1016/j.bioorg.2019.102973 Bioorganic Chemistry |
| Anti-inflammatory | inhibition | NO production | IC50=17.6 μM (NO inhibition) | 10.1016/j.bioorg.2019.102973 Bioorganic Chemistry |
| Antibacterial | MIC | methicillin-resistant Staphylococcus aureus (MRSA) | 50.0 μg/mL | 10.1016/j.bioorg.2019.102973 Bioorganic Chemistry |