SCS-C006206

pestalotiopyrone M

Pathway: Polyketides Superclass: Linear polyketides Class: Open-chain polyketides

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

Neopestalotiopsis sp. (NA)

Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Amphisphaeriales Family Sporocadaceae Genus Neopestalotiopsis Species Neopestalotiopsis sp.

South China Sea

DOI: 10.3390/md23040148 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

272.3 Da

Threshold ≤ 500

ALogP

0.79

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C14H24O5

Molecular Weight:

272.3410 Da

SMILES:

CC(=C\[C@H](C)[C@@H](C)O)/C=C(\C)C(=O)OC[C@H](O)CO

InChIKey:

                        SSRINNAXKRXUTM-NAULFRICSA-N
                        
                    

InChI:

InChI=1S/C14H24O5/c1-9(5-10(2)12(4)16)6-11(3)14(18)19-8-13(17)7-15/h5-6,10,12-13,15-17H,7-8H2,1-4H3/b9-5+,11-6+/t10-,12+,13+/m0/s1

Calculated Properties

ALogP:

0.792 lipophilicity

TPSA:

86.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

0 (0 aromatic)

Chiral Centers:

Fsp³:

0.6429 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006206

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Linear polyketides

NPClassifier Class:

Open-chain polyketides

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
Antifibrotic / Organ protection	inhibition of α-SMA expression and ECM production	TGF-β1-induced renal fibrosis	All tested compounds (1, 5–8, and 11–12) at 10 μM showed obvious anti-fibrotic activity by inhibiting TGF-β1-induced α-SMA expression and extracellular matrix production (collagen I and fibronectin).	10.3390/md23040148 Marine Drugs

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