SCS-C000381
sclerketide C
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
490.0 Da
Threshold ≤ 500
ALogP
4.54
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C26H32ClNO6
Molecular Weight:
490.0000 Da
SMILES:
CC[C@H](C)/C=C(C)/C=C/C1=CC2=C(Cl)C(=O)[C@](C)(OC(C)=O)C(=O)C2=CN1CCCC(=O)OC
InChIKey:
XWWNMYFZBOZWKF-ZGLDCBQPSA-N
InChI:
InChI=1S/C26H32ClNO6/c1-7-16(2)13-17(3)10-11-19-14-20-21(15-28(19)12-8-9-22(30)33-6)24(31)26(5,34-18(4)29)25(32)23(20)27/h10-11,13-16H,7-9,12H2,1-6H3/b11-10+,17-13+/t16-,26+/m0/s1
Calculated Properties
ALogP:
4.538 lipophilicity
TPSA:
89.98 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
7
Rotatable Bonds:
9
Ring Count:
2
(0 aromatic)
Chiral Centers:
2
Fsp³:
0.4615 fraction sp³ carbon
Database Information
Compound ID:
SCS-C000381
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 | 2.7 μM | 10.1016/j.bioorg.2019.102973 Bioorganic Chemistry |
| Anti-inflammatory | inhibition | NO production | IC50=2.7 μM (NO inhibition) | 10.1016/j.bioorg.2019.102973 Bioorganic Chemistry |
| Antitumor | IC50 | cancer cells | 14.8 μM | 10.1016/j.bioorg.2019.102973 Bioorganic Chemistry |