SCS-C008352

22-epoxyberkeleydione

Pathway: Polyketides | 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

Talaromyces purpureogenus SCSIO 41517 (NA)

Original source name: Talaromyces purpureogenus SCSIO 41517 | Talaromyces purpureogenus

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Trichocomaceae Genus Talaromyces Species Talaromyces purpureogenus

South China Sea

DOI: 10.1021/acs.jnatprod.1c00681 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

430.5 Da

Threshold ≤ 500

ALogP

2.45

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C24H30O7

Molecular Weight:

430.4970 Da

SMILES:

COC(=O)[C@@]12C(=O)[C@@](C)(O)C(=O)[C@]1(C)C[C@H]1C(C)=C3CC(=O)OC(C)(C)C3=CC[C@@]12C

InChIKey:

                        AEOAXPCYIGPTGQ-ZYKPDOIRSA-N
                        
                    

InChI:

InChI=1S/C24H30O7/c1-12-13-10-16(25)31-20(2,3)14(13)8-9-21(4)15(12)11-22(5)17(26)23(6,29)18(27)24(21,22)19(28)30-7/h8,15,29H,9-11H2,1-7H3/t15-,21-,22-,23-,24+/m0/s1

Calculated Properties

ALogP:

2.453 lipophilicity

TPSA:

106.97 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

4 (0 aromatic)

Chiral Centers:

Fsp³:

0.6667 fraction sp³ carbon

Database Information

Compound ID:

SCS-C008352

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
Metabolic / Lipid regulation	inhibitory	triglyceride accumulation	Moreover, 7-9 and 12 exhibited the activity of reducing triglyceride in 3T3-L1 adipocytes in a dosage-dependent manner.	10.1021/acs.jnatprod.1c00681 Journal of Natural Products

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