SCS-C007589
guignardone Y
Pathway: Terpenoids
Superclass: Meroterpenoids
Class: Miscellaneous meroterpenoids | Prenyl quinone meroterpenoids
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 sp. NBUF154
(soft coral-derived fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
· 60 m
DOI:
10.1002/cbdv.202200475
· Chemistry & Biodiversity
Drug-likeness (Lipinski Ro5)
Molecular Weight
360.5 Da
Threshold ≤ 500
ALogP
4.10
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C22H32O4
Molecular Weight:
360.4940 Da
SMILES:
CO[C@H]1C[C@H](O)C2=C(C[C@H]3[C@H](/C(C)=C\CC=C(C)C)CC[C@@]3(C)O2)C1=O
InChIKey:
PRXQTKPMXQDCTR-QWXCSMEJSA-N
InChI:
InChI=1S/C22H32O4/c1-13(2)7-6-8-14(3)15-9-10-22(4)17(15)11-16-20(24)19(25-5)12-18(23)21(16)26-22/h7-8,15,17-19,23H,6,9-12H2,1-5H3/b14-8-/t15-,17-,18-,19-,22+/m0/s1
Calculated Properties
ALogP:
4.097 lipophilicity
TPSA:
55.76 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
4
Ring Count:
3
(0 aromatic)
Chiral Centers:
5
Fsp³:
0.6818 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007589
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Miscellaneous meroterpenoids
Prenyl quinone meroterpenoids
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 |
|---|---|---|---|---|
| Antiviral | EC50 | human enterovirus 71 (EV71) | 1.25 μM | 10.1002/cbdv.202200475 Chemistry & Biodiversity |
| Antibacterial | inhibition | ten Vibrio strains (including V. parahaemolyticus NBUV004, P. damselae NBUV007, etc.) | Compounds 1–8 were found to display no inhibition against these pathogens. | 10.1002/cbdv.202200475 Chemistry & Biodiversity |