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  3. (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-5-methoxy-3,4-dimethyl-2-benzofuran-1-one

SCS-C005315

(3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-5-methoxy-3,4-dimethyl-2-benzofuran-1-one

Pathway: Shikimates and Phenylpropanoids Superclass: Coumarins Class: Isocoumarins
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Chemical Structure

Structure of (3R)-7-hydroxy-3-[(1R)-1-hydroxyethyl]-5-methoxy-3,4-dimethyl-2-benzofuran-1-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

Xylaria sp. (gorgonian-derived fungus)
Kingdom Fungi Phylum Ascomycota Class Sordariomycetes Order Xylariales Family Xylariaceae Genus Xylaria Species NA
Yangjiang
DOI: 10.1177/1934578x1200701022  · Natural Product Communications

Drug-likeness (Lipinski Ro5)

Molecular Weight
252.3 Da
Threshold ≤ 500
ALogP
1.48
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C13H16O5
Molecular Weight:
252.2660 Da
SMILES:
COc1cc(O)c2c(c1C)[C@](C)([C@@H](C)O)OC2=O
InChIKey:
YKQYIQHWWYVPHK-UHLUBPPHSA-N
InChI:
InChI=1S/C13H16O5/c1-6-9(17-4)5-8(15)10-11(6)13(3,7(2)14)18-12(10)16/h5,7,14-15H,1-4H3/t7-,13+/m1/s1
Calculated Properties
ALogP:
1.476 lipophilicity
TPSA:
75.99 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
5
Rotatable Bonds:
2
Ring Count:
2 (1 aromatic)
Chiral Centers:
2
Fsp³:
0.4615 fraction sp³ carbon

Database Information

Compound ID:
SCS-C005315
NPClassifier Pathway:
Shikimates and Phenylpropanoids
NPClassifier Superclass:
Coumarins
NPClassifier Class:
Isocoumarins
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD22269

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged