4-[6-(4-Hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol

Details

• Internal ID: cca5bed2-857a-47ac-a22c-dba205c9f994
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 4-[6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
• InChI: InChI=1S/C20H22O6/c1-23-17-7-11(3-5-15(17)21)19-13-9-26-20(14(13)10-25-19)12-4-6-16(22)18(8-12)24-2/h3-8,13-14,19-22H,9-10H2,1-2H3
• InChI Key: HGXBRUKMWQGOIE-UHFFFAOYSA-N
• Popularity: 947 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.40 g/mol
• Exact Mass: 358.14163842 g/mol
• Topological Polar Surface Area (TPSA): 77.40 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 3.19
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• (+/-)-PINORESINOL
• 4263-88-1
• 7452-03-1
• 4,4'-(Hexahydrofuro[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol)
• NSC35444
• 4-[6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
• 4,4'-[Hexahydrofuro[3,4-c]furan-1,4-diyl]bis(2-methoxyphenol)
• 10061-38-8
• 4-[(3S,3aR,6S,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
• bmse010297
• 3,3'-Bisdemethylpinoresinol
• SCHEMBL122106
• CHEMBL2252392
• HMS3347E17
• FT-0775687
• H1692
• D91065
• B0005-188759
• 4,4'-[(1S,3aR,4S,6aR)-Tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis(2-methoxyphenol)
• (+)-Pinoresinol, 4,4'-((1S,3aR,4S,6aR)-Hexahydrofuro[3,4-c]furan-1,4-diyl)bis(2-methoxyphenol)
• 4-[(3As,6aR)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
• Phenol,4'-(tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl)bis[2-methoxy-, [1S-(1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9843	98.43%
Caco-2	+	0.5739	57.39%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8501	85.01%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9489	94.89%
OATP1B3 inhibitior	+	0.9620	96.20%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5745	57.45%
P-glycoprotein inhibitior	+	0.7049	70.49%
P-glycoprotein substrate	-	0.9544	95.44%
CYP3A4 substrate	-	0.5668	56.68%
CYP2C9 substrate	-	0.7850	78.50%
CYP2D6 substrate	+	0.4564	45.64%
CYP3A4 inhibition	+	0.5791	57.91%
CYP2C9 inhibition	+	0.7854	78.54%
CYP2C19 inhibition	+	0.8327	83.27%
CYP2D6 inhibition	-	0.7042	70.42%
CYP1A2 inhibition	+	0.5398	53.98%
CYP2C8 inhibition	-	0.5604	56.04%
CYP inhibitory promiscuity	+	0.8740	87.40%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8908	89.08%
Carcinogenicity (trinary)	Non-required	0.4805	48.05%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.6712	67.12%
Skin irritation	-	0.8265	82.65%
Skin corrosion	-	0.9656	96.56%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7564	75.64%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.7470	74.70%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8549	85.49%
Acute Oral Toxicity (c)	III	0.6806	68.06%
Estrogen receptor binding	+	0.8354	83.54%
Androgen receptor binding	+	0.7085	70.85%
Thyroid receptor binding	+	0.7482	74.82%
Glucocorticoid receptor binding	+	0.6976	69.76%
Aromatase binding	-	0.5820	58.20%
PPAR gamma	+	0.5367	53.67%
Honey bee toxicity	-	0.9286	92.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9731	97.31%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.31%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.84%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.44%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.89%	97.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.29%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.65%	86.33%
CHEMBL3438	Q05513	Protein kinase C zeta	84.65%	88.48%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.96%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.79%	85.14%
CHEMBL2535	P11166	Glucose transporter	82.48%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.12%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.11%	92.62%
CHEMBL1951	P21397	Monoamine oxidase A	81.94%	91.49%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.87%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.63%	89.00%
CHEMBL4208	P20618	Proteasome component C5	80.70%	90.00%
CHEMBL2581	P07339	Cathepsin D	80.65%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.15%	99.17%

Plants that contains it

• Abies nephrolepis
• Abies spectabilis
• Aconitum carmichaelii
• Aconitum japonicum
• Anastatica hierochuntica
• Araucaria angustifolia
• Arnica mollis
• Artemisia arborescens
• Asarum sieboldii
• Asparagus officinalis
• Balanophora abbreviata
• Balanophora fungosa
• Balanophora japonica
• Balanophora papuana
• Berberis koreana
• Bhesa paniculata
• Brassica fruticulosa
• Breynia vitis-idaea
• Brucea javanica
• Bupleurum salicifolium
• Camellia sinensis
• Catunaregam spinosa
• Centaurea calcitrapa
• Colocasia antiquorum
• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Daphne feddei
• Daphne genkwa
• Daphne giraldii
• Daphne mezereum
• Dendrobium loddigesii
• Dendrobium plicatile
• Eucommia ulmoides
• Euterpe oleracea
• Fagraea blumei
• Fagraea racemosa
• Forsythia giraldiana
• Forsythia suspensa
• Forsythia viridissima
• Gnetum montanum
• Gymnadenia conopsea
• Hedyotis lawsoniae
• Helianthus annuus
• Helicteres angustifolia
• Helicteres hirsuta
• Ipomoea nil
• Ipomoea purpurea
• Isatis tinctoria
• Linum album
• Linum usitatissimum
• Lonicera morrowii
• Magnolia biondii
• Magnolia coco
• Melia azedarach
• Mikania haenkeana
• Mitragyna speciosa
• Morinda citrifolia
• Nardostachys jatamansi
• Pandanus boninensis
• Pandanus tectorius
• Peperomia blanda
• Persicaria tinctoria
• Phlomoides hamosa
• Phyllanthus oxyphyllus
• Picea abies
• Picea glauca
• Picea glehnii
• Pinus armandii
• Pulsatilla chinensis
• Punica granatum
• Rhaphidophora decursiva
• Rubia yunnanensis
• Sambucus adnata
• Sambucus nigra
• Sambucus williamsii
• Saussurea laniceps
• Saussurea medusa
• Sesamum indicum
• Simira eliezeriana
• Solanum nigrum
• Sonchus macrocarpus
• Stellera chamaejasme
• Strophanthus gratus
• Stuckenia pectinata
• Symplocos glomerata
• Syzygium cumini
• Thuja occidentalis
• Valeriana microphylla
• Viburnum foetidum
• Viscum coloratum
• Vitex negundo
• Wikstroemia canescens
• Wikstroemia hainanensis
• Wisteria floribunda
• Xanthium strumarium
• Zantedeschia aethiopica
• Zanthoxylum ailanthoides
• Zanthoxylum beecheyanum
• Zanthoxylum simulans

Cross-Links

• PubChem: 234817
• NPASS: NPC158079
• LOTUS: LTS0011247
• wikiData: Q104167841