SCS-C005828

purpurogenolide C

Pathway: Polyketides | Terpenoids Superclass: Meroterpenoids Class: Tetraketide meroterpenoids

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=C1C2=CC(=O)OC(C)(C)C2=CC[C@@]2(C)[C@H]1C[C@@]1(C)C(=O)O[C@H]3O[C@H](C)C(=O)[C@]2(C(=O)OC)[C@H]31

InChIKey:

                        CELLGHOJUHAKBM-PXZNHALXSA-N
                        
                    

InChI:

InChI=1S/C26H30O8/c1-12-14-10-17(27)34-23(3,4)15(14)8-9-25(6)16(12)11-24(5)18-20(33-21(24)29)32-13(2)19(28)26(18,25)22(30)31-7/h8,10,13,16,18,20H,1,9,11H2,2-7H3/t13-,16+,18-,20-,24-,25+,26+/m1/s1

Calculated Properties

ALogP:

2.813 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-C005828

NPClassifier Pathway:

Polyketides 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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