SCS-C005839

purpurogenolide A

Pathway: Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids

Chemical Structure

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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

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

426.5 Da

Threshold ≤ 500

ALogP

3.43

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C25H30O6

Molecular Weight:

426.5090 Da

SMILES:

CC1=C2CC(=O)OC(C)(C)C2=CC[C@@]2(C)[C@H]1C[C@@]1(C)C(=O)[C@]3(C)C[C@@]24C(=O)OC[C@]41O3

InChIKey:

                        LVMPBZHNRWORRO-ZGRHUMCPSA-N
                        
                    

InChI:

InChI=1S/C25H30O6/c1-13-14-9-17(26)30-20(2,3)15(14)7-8-21(4)16(13)10-22(5)18(27)23(6)11-24(21)19(28)29-12-25(22,24)31-23/h7,16H,8-12H2,1-6H3/t16-,21-,22-,23-,24+,25+/m0/s1

Calculated Properties

ALogP:

3.435 lipophilicity

TPSA:

78.90 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (0 aromatic)

Chiral Centers:

Fsp³:

0.7200 fraction sp³ carbon

Database Information

Compound ID:

SCS-C005839

NPClassifier Pathway:

Terpenoids

NPClassifier Superclass:

Meroterpenoids

NPClassifier Class:

Tetraketide meroterpenoids

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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