SCS-C007541
(3R,4S)-3,4,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one
Pathway: Polyketides
Superclass: Naphthalenes
Class: Naphthalenones
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
194.2 Da
Threshold ≤ 500
ALogP
0.37
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C10H10O4
Molecular Weight:
194.1860 Da
SMILES:
O=C1C[C@@H](O)[C@@H](O)c2cccc(O)c21
InChIKey:
HPIFRXWPEZBFHJ-SCZZXKLOSA-N
InChI:
InChI=1S/C10H10O4/c11-6-3-1-2-5-9(6)7(12)4-8(13)10(5)14/h1-3,8,10-11,13-14H,4H2/t8-,10+/m1/s1
Calculated Properties
ALogP:
0.373 lipophilicity
TPSA:
77.76 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
4
Rotatable Bonds:
0
Ring Count:
2
(1 aromatic)
Chiral Centers:
2
Fsp³:
0.3000 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007541
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Naphthalenes
NPClassifier Class:
Naphthalenones
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... without cytotoxicity to RAW264.7 cells within 50 μM. | 10.1002/cbdv.202000192 Chemistry & Biodiversity |
| Anti-inflammatory | IC50 | LPS-induced NO production | 44.7 μM | 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 |