SCS-C005817

penilarane D

Pathway: Terpenoids

Chemical Structure

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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

494.9 Da

Threshold ≤ 500

ALogP

1.09

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H27ClO9

Molecular Weight:

494.9240 Da

SMILES:

C[C@H]1O[C@@H]2OC(=O)[C@]3(C)C[C@@H]4[C@]5(C)[C@@H](C=C6C(=CC(=O)OC6(C)C)[C@@]4(O)CCl)O[C@]14O[C@]45[C@]23O

InChIKey:

                        NZDWLHZZZXCMFW-YCUQDCGSSA-N
                        
                    

InChI:

InChI=1S/C24H27ClO9/c1-10-23-24(34-23)20(5)13(8-19(4)16(27)31-17(30-10)22(19,24)29)21(28,9-25)12-7-15(26)33-18(2,3)11(12)6-14(20)32-23/h6-7,10,13-14,17,28-29H,8-9H2,1-5H3/t10-,13-,14-,17-,19+,20-,21+,22+,23+,24-/m1/s1

Calculated Properties

ALogP:

1.087 lipophilicity

TPSA:

124.05 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (0 aromatic)

Chiral Centers:

Fsp³:

0.7500 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005817

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

N/A

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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