SCS-C006175

(R)-3-Hydroxy-1-[(S)-4-hydroxy-1,3-dihydroisobenzofuran-1-yl]butan-2-one

Pathway: Polyketides Superclass: Cyclic polyketides Class: Phthalide derivatives

Chemical Structure

Structure of (R)-3-Hydroxy-1-[(S)-4-hydroxy-1,3-dihydroisobenzofuran-1-yl]butan-2-one

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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

Pestalotiopsis heterocornis XWS03F09 (sponge)

Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Amphisphaeriales Family Sporocadaceae Genus Pestalotiopsis Species Pestalotiopsis heterocornis

South China Sea

DOI: 10.3390/molecules24142655 · Molecules

Drug-likeness (Lipinski Ro5)

Molecular Weight

222.2 Da

Threshold ≤ 500

ALogP

1.30

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C12H14O4

Molecular Weight:

222.2400 Da

SMILES:

C[C@@H](O)C(=O)C[C@H]1OCc2c(O)cccc21

InChIKey:

                        BBGDMJGYFNHPDK-JMCQJSRRSA-N
                        
                    

InChI:

InChI=1S/C12H14O4/c1-7(13)11(15)5-12-8-3-2-4-10(14)9(8)6-16-12/h2-4,7,12-14H,5-6H2,1H3/t7-,12-/m1/s1

Calculated Properties

ALogP:

1.304 lipophilicity

TPSA:

66.76 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (1 aromatic)

Chiral Centers:

Fsp³:

0.4167 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006175

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Cyclic polyketides

NPClassifier Class:

Phthalide derivatives

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	IC50	human cancer cell lines (Ichikawa, BGC-823, HepG2, 7860)	20.4–94.2 μM	10.3390/molecules24142655 Molecules

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