SCS-C005833
peniscmeroterpenoid J
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
508.6 Da
Threshold ≤ 500
ALogP
2.81
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C27H40O9
Molecular Weight:
508.6080 Da
SMILES:
COC(=O)CC[C@@]1(C)[C@@H]2C[C@@]3(C)C(=O)[C@@](C)(C(=O)OC)O[C@H]4OC(=O)[C@H]([C@H]43)[C@@]2(C)CC[C@@H]1C(C)(C)O
InChIKey:
YMRJXAUQTKMALO-YFWHMRMFSA-N
InChI:
InChI=1S/C27H40O9/c1-23(2,32)14-9-11-25(4)15(24(14,3)12-10-16(28)33-7)13-26(5)18-17(25)19(29)35-20(18)36-27(6,21(26)30)22(31)34-8/h14-15,17-18,20,32H,9-13H2,1-8H3/t14-,15+,17+,18-,20-,24-,25+,26-,27+/m1/s1
Calculated Properties
ALogP:
2.806 lipophilicity
TPSA:
125.43 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
9
Rotatable Bonds:
5
Ring Count:
4
(0 aromatic)
Chiral Centers:
9
Fsp³:
0.8519 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005833
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 |