4-[(3S,3aR,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenol

Details

• Internal ID: fa000ba3-c8c9-4832-84e0-bdfad32da5f7
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 4-[(3S,3aR,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenol
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)C2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC(=C(C=C4)O)OC
• InChI: InChI=1S/C21H24O7/c1-24-16-6-11(4-5-15(16)22)20-13-9-28-21(14(13)10-27-20)12-7-17(25-2)19(23)18(8-12)26-3/h4-8,13-14,20-23H,9-10H2,1-3H3/t13-,14-,20+,21?/m0/s1
• InChI Key: VJOBNGRIBLNUKN-ITZZLVQVSA-N
• Popularity: 16 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.15220310 g/mol
• Topological Polar Surface Area (TPSA): 86.60 Ų
• XlogP: 2.30

Synonyms

• CHEMBL513023
• 4-[(3S,3aR,6aR)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenol
• (-) Medioresinol
• D00RGP
• BDBM50259877
• NSC329245
• NSC-329245

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	13700 nM	IC50	PMID: 15679319

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.52%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.49%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.29%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.32%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.89%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.26%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.22%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.01%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.77%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.46%	99.15%
CHEMBL3438	Q05513	Protein kinase C zeta	84.35%	88.48%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.52%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.94%	91.49%
CHEMBL2581	P07339	Cathepsin D	81.93%	98.95%
CHEMBL4208	P20618	Proteasome component C5	81.04%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.15%	99.17%

Plants that contains it

• Ananas comosus
• Bupleurum salicifolium
• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Dirca occidentalis
• Gardenia jasminoides
• Hibiscus cannabinus
• Isatis tinctoria
• Ophryosporus lorentzii
• Peperomia heyneana
• Piper cubeba
• Saccharum officinarum
• Solanum nigrum
• Spatholobus suberectus
• Vaccinium vitis-idaea

Cross-Links

• PubChem: 332425
• NPASS: NPC99572
• ChEMBL: CHEMBL513023
• LOTUS: LTS0041035
• wikiData: Q104401593