SCS-C006574

Pestaphilone J

Pathway: Polyketides Superclass: Chromanes Class: Azaphilones

Chemical Structure

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Source Information

Neopestalotiopsis sp. (NA)

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

South China Sea · longitude of 108.87 and a latitude of 21.74

DOI: 10.3390/md22060241 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

362.4 Da

Threshold ≤ 500

ALogP

1.53

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C20H26O6

Molecular Weight:

362.4220 Da

SMILES:

CC[C@H](C)/C=C1\CO[C@](C)(C2=CC3=CC(=O)[C@@](C)(O)[C@H](O)C3=CO2)[C@@H]1O

InChIKey:

                        PUGDICUHPSFBCO-PMMBDWCPSA-N
                        
                    

InChI:

InChI=1S/C20H26O6/c1-5-11(2)6-13-9-26-20(4,17(13)22)16-8-12-7-15(21)19(3,24)18(23)14(12)10-25-16/h6-8,10-11,17-18,22-24H,5,9H2,1-4H3/b13-6+/t11-,17+,18+,19+,20+/m0/s1

Calculated Properties

ALogP:

1.528 lipophilicity

TPSA:

96.22 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (0 aromatic)

Chiral Centers:

Fsp³:

0.5500 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006574

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Chromanes

NPClassifier Class:

Azaphilones

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
Angiogenesis modulation	—	intersomitic vessel formation	40.0 μM	10.3390/md22060241 Marine Drugs
Antibacterial	MIC	Staphylococcus aureus	64.0 μg/mL	10.3390/md22060241 Marine Drugs
Antitumor	—	HepG2; A549; HCT116; Hela; MCF-7	In the cytotoxic assay, all of the compounds were inactive against the HepG2, A549, HCT116, Hela, MCF-7, and L02 cell lines.	10.3390/md22060241 Marine Drugs

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