SCS-C005837
peniscmeroterpenoid C
Pathway: Terpenoids
Superclass: Meroterpenoids
Class: Tetraketide meroterpenoids
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 sp. F0836
(soft coral-derived fungus)
Original source name: Penicillium sp. (strain F0836)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
NA
South China Sea
· -670m
· 115.1896°E, 20.0887°N
DOI:
10.1021/acs.jmedchem.5c03055
· Journal of Medicinal Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
476.6 Da
Threshold ≤ 500
ALogP
3.52
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
7
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C26H36O8
Molecular Weight:
476.5660 Da
SMILES:
C=C(C)[C@H]1CC[C@@]2(C)[C@@H](C[C@@]3(C)C(=O)[C@@](C)(C(=O)OC)O[C@H]4OC(=O)[C@@H]2[C@H]43)[C@]1(C)CCC(=O)O
InChIKey:
GFERZDFHKQXUTD-HLTVEIOUSA-N
InChI:
InChI=1S/C26H36O8/c1-13(2)14-8-10-24(4)15(23(14,3)11-9-16(27)28)12-25(5)18-17(24)19(29)33-20(18)34-26(6,21(25)30)22(31)32-7/h14-15,17-18,20H,1,8-12H2,2-7H3,(H,27,28)/t14-,15+,17+,18-,20-,23-,24+,25-,26+/m1/s1
Calculated Properties
ALogP:
3.522 lipophilicity
TPSA:
116.20 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
7
Rotatable Bonds:
5
Ring Count:
4
(0 aromatic)
Chiral Centers:
9
Fsp³:
0.7692 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005837
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Meroterpenoids
NPClassifier Class:
Tetraketide 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 |
|---|---|---|---|---|
| Receptor / Signaling modulation | inhibition | TGF-β1/Smad signaling; HSF1/AMPK metabolic axis | 10.0 μM | 10.1021/acs.jmedchem.5c03055 Journal of Medicinal Chemistry |