SCS-C000384
sequoiatone B
Pathway: Polyketides
Superclass: Chromanes
Class: Azaphilones
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 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
374.5 Da
Threshold ≤ 500
ALogP
4.14
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H30O5
Molecular Weight:
374.5000 Da
SMILES:
CCCCCC[C@@H](C)C(=O)/C=C1/C(C(=O)OC)=C2C=C(C)OC=C2[C@@]1(C)O
InChIKey:
AZRKTTNHSKOLMR-ZFKUNJMVSA-N
InChI:
InChI=1S/C22H30O5/c1-6-7-8-9-10-14(2)19(23)12-17-20(21(24)26-5)16-11-15(3)27-13-18(16)22(17,4)25/h11-14,25H,6-10H2,1-5H3/b17-12-/t14-,22+/m1/s1
Calculated Properties
ALogP:
4.141 lipophilicity
TPSA:
72.83 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
5
Rotatable Bonds:
8
Ring Count:
2
(0 aromatic)
Chiral Centers:
2
Fsp³:
0.5455 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000384
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 | 5.2 μM | 10.1016/j.bioorg.2019.102973 Bioorganic Chemistry |