SCS-C007538
(2S,4R,2'S,4'R)-4,4'-oxybis(5-methoxy-2-methyl-3,4-dihydro-2H-1-benzopyran)
Pathway: Polyketides
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 citrinum QJF-22
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium citrinum
South China Sea
DOI:
10.1002/cbdv.202000192
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
370.4 Da
Threshold ≤ 500
ALogP
4.84
Threshold ≤ 5
H-Bond Donors
0
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H26O5
Molecular Weight:
370.4450 Da
SMILES:
COc1cccc2c1[C@H](O[C@@H]1C[C@H](C)Oc3cccc(OC)c31)C[C@H](C)O2
InChIKey:
WYGWBWYDNRLBJN-AFHBHXEDSA-N
InChI:
InChI=1S/C22H26O5/c1-13-11-19(21-15(23-3)7-5-9-17(21)25-13)27-20-12-14(2)26-18-10-6-8-16(24-4)22(18)20/h5-10,13-14,19-20H,11-12H2,1-4H3/t13-,14-,19+,20+/m0/s1
Calculated Properties
ALogP:
4.845 lipophilicity
TPSA:
46.15 Ų polar surface area
H-Bond Donors:
0
H-Bond Acceptors:
5
Rotatable Bonds:
4
Ring Count:
4
(2 aromatic)
Chiral Centers:
4
Fsp³:
0.4545 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007538
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
N/A
NPClassifier Class:
N/A
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 | — | MDA-MB-435; A549 human cell lines | Compounds 1–6 were evaluated for their cytotoxicity against MDA-MB-435 and A549 human cell lines... However, only compound 6 displayed moderate anti-inflammatory activity | 10.1002/cbdv.202000192 Chemistry & Biodiversity |
| Anti-inflammatory | — | LPS-induced NO production | — Structured numeric value is not available in this record; see the primary reference. | 10.1002/cbdv.202000192 Chemistry & Biodiversity |
| Enzyme inhibition | IC50 | acetylcholinesterase | > 100.0 μM | 10.1002/cbdv.202000192 Chemistry & Biodiversity |
| Enzyme inhibition | IC50 | α-glucosidase | > 100.0 μM | 10.1002/cbdv.202000192 Chemistry & Biodiversity |
| Antioxidant | IC50 | DPPH free radical | > 100.0 μM | 10.1002/cbdv.202000192 Chemistry & Biodiversity |