SCS-C007945

talaroterphenyl A

Pathway: Shikimates and Phenylpropanoids Superclass: Terphenyls Class: p-Terphenyls

Chemical Structure

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Download: SDF SMILES

Source Information

Talaromyces sp. SCSIO 41412 (soft coral-derived fungus)

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

South China Sea

DOI: 10.1021/acs.jnatprod.4c00422 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

364.4 Da

Threshold ≤ 500

ALogP

4.67

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H20O5

Molecular Weight:

364.3970 Da

SMILES:

COc1c(O)c(-c2ccccc2)c(OC(C)=O)c(OC)c1-c1ccccc1

InChIKey:

                        XCKVBIHQDKUVFG-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C22H20O5/c1-14(23)27-22-17(15-10-6-4-7-11-15)19(24)20(25-2)18(21(22)26-3)16-12-8-5-9-13-16/h4-13,24H,1-3H3

Calculated Properties

ALogP:

4.669 lipophilicity

TPSA:

64.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (3 aromatic)

Chiral Centers:

Fsp³:

0.1364 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007945

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

Terphenyls

NPClassifier Class:

p-Terphenyls

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
Enzyme inhibition	IC50	phosphodiesterase 4 (PDE4)	— Structured numeric value is not available in this record; see the primary reference.	10.1021/acs.jnatprod.4c00422 Journal of Natural Products
Anti-inflammatory	—	pro-inflammatory cytokines IL-6; TNF-α	Talaroterphenyl A (1), with a low cytotoxicity, showed obvious anti-inflammatory activity in LPS-stimulated RAW264.7 cells.	10.1021/acs.jnatprod.4c00422 Journal of Natural Products
Antifibrotic / Organ protection	—	FN1, COL1, α-SMA expression	5.0–20.0 μM	10.1021/acs.jnatprod.4c00422 Journal of Natural Products

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