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SCS-C006174

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

Pathway: Polyketides Superclass: Cyclic polyketides Class: Phthalide derivatives
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Chemical Structure

Structure of (R)-3-Hydroxy-1-[(R)-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
2
Threshold ≤ 5
H-Bond Acceptors
4
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-KRTXAFLBSA-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 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
4
Rotatable Bonds:
3
Ring Count:
2 (1 aromatic)
Chiral Centers:
2
Fsp³:
0.4167 fraction sp³ carbon

Database Information

Compound ID:
SCS-C006174
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Cyclic polyketides
NPClassifier Class:
Phthalide derivatives
Glycoside:
No
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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Structure enlarged