SCS-C000714

3-hydroxy-5-[[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]methyl]-4-(4-hydroxyphenyl)-(5H)-furan-one

Pathway: Shikimates and Phenylpropanoids Superclass: Diazotetronic acids and derivatives | Lignans Class: Neolignans | Pulvinones

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Chemical Structure

Structure of 3-hydroxy-5-[[4-hydroxy-3-(3-methyl-2-buten-1-yl)phenyl]methyl]-4-(4-hydroxyphenyl)-(5H)-furan-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

Aspergillus terreus Y10 (mangrove endophytic fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Aspergillus Species Aspergillus terreus

Hainan Island

DOI: 10.3390/md16110428 · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight

366.4 Da

Threshold ≤ 500

ALogP

4.04

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C22H22O5

Molecular Weight:

366.4100 Da

SMILES:

CC(C)=CCc1cc(C[C@H]2OC(=O)C(O)=C2c2ccc(O)cc2)ccc1O

InChIKey:

                        SDUGYQDMSWYSGN-LJQANCHMSA-N
                        
                    

InChI:

InChI=1S/C22H22O5/c1-13(2)3-5-16-11-14(4-10-18(16)24)12-19-20(21(25)22(26)27-19)15-6-8-17(23)9-7-15/h3-4,6-11,19,23-25H,5,12H2,1-2H3/t19-/m1/s1

Calculated Properties

ALogP:

4.044 lipophilicity

TPSA:

86.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (2 aromatic)

Chiral Centers:

Fsp³:

0.2273 fraction sp³ carbon

Database Information

Compound ID:

SCS-C000714

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

Diazotetronic acids and derivatives Lignans

NPClassifier Class:

Neolignans Pulvinones

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
Anti-inflammatory	IC50	LPS-induced BV2 microglial cells	9.9 μg/mL	10.3390/md16110428 Marine Drugs

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