SCS-C005814
penilarane A
Pathway: Polyketides | 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
506.9 Da
Threshold ≤ 500
ALogP
1.75
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
9
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C25H27ClO9
Molecular Weight:
506.9350 Da
SMILES:
C[C@H]1OC(=O)[C@@]23[C@@H]4[C@H]5OC(=O)[C@]4(C)C[C@@H]4[C@]2(C)[C@H](C=C2C(=CC(=O)OC2(C)C)[C@@]4(O)CCl)O[C@@]13O5
InChIKey:
QTFIELICSYJQDR-QLEHVBHISA-N
InChI:
InChI=1S/C25H27ClO9/c1-10-25-24(19(29)31-10)16-17(35-25)32-18(28)21(16,4)8-13-22(24,5)14(33-25)6-11-12(23(13,30)9-26)7-15(27)34-20(11,2)3/h6-7,10,13-14,16-17,30H,8-9H2,1-5H3/t10-,13-,14+,16-,17+,21-,22-,23+,24+,25-/m1/s1
Calculated Properties
ALogP:
1.747 lipophilicity
TPSA:
117.59 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
9
Rotatable Bonds:
1
Ring Count:
7
(0 aromatic)
Chiral Centers:
10
Fsp³:
0.7200 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005814
NPClassifier Pathway:
Polyketides
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 |