SCS-C006166
penicillin-like compound
Pathway: Shikimates and Phenylpropanoids
Superclass: Coumarins
Class: Simple coumarins
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
Aspergillus spelaeus
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus spelaeus
South China Sea
· 21.573° N, 109.767° E
DOI:
10.3390/md23060251
· Marine Drugs
Drug-likeness (Lipinski Ro5)
Molecular Weight
450.8 Da
Threshold ≤ 500
ALogP
1.16
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C20H19ClN2O8
Molecular Weight:
450.8310 Da
SMILES:
COc1ccc2cc(NC(=O)C3=NO[C@H]4[C@H](O)C=C[C@@H](Cl)[C@@]4(O)C3)c(=O)oc2c1OC
InChIKey:
ROOWAKADKHUVSQ-OVCSSCHWSA-N
InChI:
InChI=1S/C20H19ClN2O8/c1-28-13-5-3-9-7-10(19(26)30-15(9)16(13)29-2)22-18(25)11-8-20(27)14(21)6-4-12(24)17(20)31-23-11/h3-7,12,14,17,24,27H,8H2,1-2H3,(H,22,25)/t12-,14-,17+,20+/m1/s1
Calculated Properties
ALogP:
1.163 lipophilicity
TPSA:
139.82 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
9
Rotatable Bonds:
4
Ring Count:
4
(2 aromatic)
Chiral Centers:
4
Fsp³:
0.3500 fraction sp³ carbon
Database Information
Compound ID:
SCS-C006166
NPClassifier Pathway:
Shikimates and Phenylpropanoids
NPClassifier Superclass:
Coumarins
NPClassifier Class:
Simple coumarins
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 |
|---|---|---|---|---|
| Enzyme inhibition | inhibition rate | PDE4 | compounds 2, 3, 5, 8, 9, 11–14, and 16 exhibited weak PDE4 inhibitory activity at a concentration of 10 μM | 10.3390/md23060251 Marine Drugs |
| Antitumor | IC50 | A549 cancer cell lines | 3.4–23.7 μM | 10.3390/md23060251 Marine Drugs |