SCS-C005819

penilarane F

Pathway: Terpenoids Superclass: Diterpenoids

Chemical Structure

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Download: SDF SMILES

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

470.5 Da

Threshold ≤ 500

ALogP

2.81

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C26H30O8

Molecular Weight:

470.5180 Da

SMILES:

C=C(C)C1=CC[C@@]2(C)[C@@H](C[C@@]3(C)C(=O)O[C@H]4O[C@H](C)C(=O)[C@]2(C(=O)OC)[C@H]43)C2=C1CC(=O)OC2

InChIKey:

                        RFDLDJSWOWRXJB-MUHCSLSUSA-N
                        
                    

InChI:

InChI=1S/C26H30O8/c1-12(2)14-7-8-25(5)17(16-11-32-18(27)9-15(14)16)10-24(4)19-21(34-22(24)29)33-13(3)20(28)26(19,25)23(30)31-6/h7,13,17,19,21H,1,8-11H2,2-6H3/t13-,17+,19-,21-,24-,25+,26+/m1/s1

Calculated Properties

ALogP:

2.815 lipophilicity

TPSA:

105.20 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (0 aromatic)

Chiral Centers:

Fsp³:

0.6154 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005819

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Diterpenoids

NPClassifier Class:

N/A

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas

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

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