SCS-C000449

alternatone A

Pathway: Polyketides Superclass: Naphthalenes Class: Bisnaphthalenes

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

Alternaria alternata (marine-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Dothideomycetes Order Pleosporales Family Pleosporaceae Genus Alternaria Species Alternaria alternata

South China Sea

DOI: 10.1021/acs.jnatprod.9b00905 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

336.3 Da

Threshold ≤ 500

ALogP

2.35

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C20H16O5

Molecular Weight:

336.3000 Da

SMILES:

O=C1C[C@@H]2[C@@H]3C(=O)c4c(O)cccc4[C@@H]([C@@H]3O)[C@@H]2c2cccc(O)c21

InChIKey:

                        JGTRUZSFUZQJBG-NEUAYCJXSA-N
                        
                    

InChI:

InChI=1S/C20H16O5/c21-11-5-1-3-8-14-10(7-13(23)15(8)11)18-19(24)16-9(17(14)20(18)25)4-2-6-12(16)22/h1-6,10,14,17-18,20-22,25H,7H2/t10-,14+,17+,18+,20-/m0/s1

Calculated Properties

ALogP:

2.355 lipophilicity

TPSA:

94.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

5 (2 aromatic)

Chiral Centers:

Fsp³:

0.3000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000449

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Naphthalenes

NPClassifier Class:

Bisnaphthalenes

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
Antitumor	—	HepG-2	active against human hepatoma carcinoma HepG-2 cell line	10.1021/acs.jnatprod.9b00905 Journal of Natural Products

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