1,4-Bis(3,4,5-trimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan

Details

• Internal ID: 921ba5d0-8255-4d5e-947f-82c905d29739
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 3,6-bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)C2C3COC(C3CO2)C4=CC(=C(C(=C4)OC)OC)OC
• InChI: InChI=1S/C24H30O8/c1-25-17-7-13(8-18(26-2)23(17)29-5)21-15-11-32-22(16(15)12-31-21)14-9-19(27-3)24(30-6)20(10-14)28-4/h7-10,15-16,21-22H,11-12H2,1-6H3
• InChI Key: HRLFUIXSXUASEX-UHFFFAOYSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₀O₈
• Molecular Weight: 446.50 g/mol
• Exact Mass: 446.19406791 g/mol
• Topological Polar Surface Area (TPSA): 73.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.81
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

• SMR000440663
• 3,6-bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan
• 1,4-Bis(3,4,5-trimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan
• 80780-43-4
• NSC 172767
• Compound NP-002027
• cid_99091
• MEGxp0_000712
• MEGxp0_001362
• CHEMBL1412125
• SCHEMBL17385625
• ACon1_000778
• BDBM69394
• DTXSID40868888
• CHEBI:182352
• HRLFUIXSXUASEX-UHFFFAOYSA-N
• (+)-O,O-Dimethyl lirioresinol-B
• HMS2268L24
• 1H,3H-Furo[3,4-c]furan, 3a.alpha.,4,6,6a.alpha.-tetrahydro-1.alpha.,4.alpha.-bis(3,4,5-trimethoxyphenyl)-
• 1H,3H-Furo[3,4-c]furan, tetrahydro-1,4-bis(3,4,5-trimethoxyphenyl)-, [1S-(1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)]-
• NSC83441
• NSC-83441
• NSC172767
• AKOS040740015
• NSC-172767
• NCGC00169368-01
• BRD-A34855957-001-01-5
• O(C)c1cc(cc(OC)c1OC)C2OCC3C(OCC23)c4cc(OC)c(OC)c(OC)c4
• 3,6-bis(3,4,5-trimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrouro[3,4-c]uran
• 1,4-Bis(3,4,5-trimethoxyphenyl)-3,3a,6,6a-tetrahydro-1H,4H-furo[3,4-c]furan
• 1,4-Bis(3,4,5-trimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-, (1S,3aR,4S,6aR)-
• 1H,3H-Furo[3,4-c]furan, tetrahydro-1,4-bis(3,4,5-trimethoxyphenyl)-, (1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)-
• 1H,3H-Furo[3,4-c]furan, tetrahydro-1,4-bis(3,4,5-trimethoxyphenyl)-, (1.alpha.,3a.alpha.,4.alpha.,6a.alpha.)-(+)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9938	99.38%
Caco-2	+	0.6370	63.70%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7745	77.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9612	96.12%
OATP1B3 inhibitior	+	0.9802	98.02%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.9011	90.11%
P-glycoprotein inhibitior	+	0.7731	77.31%
P-glycoprotein substrate	-	0.9512	95.12%
CYP3A4 substrate	-	0.5666	56.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4686	46.86%
CYP3A4 inhibition	+	0.7070	70.70%
CYP2C9 inhibition	+	0.7341	73.41%
CYP2C19 inhibition	+	0.8625	86.25%
CYP2D6 inhibition	-	0.8058	80.58%
CYP1A2 inhibition	+	0.6585	65.85%
CYP2C8 inhibition	-	0.6156	61.56%
CYP inhibitory promiscuity	+	0.9013	90.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9108	91.08%
Carcinogenicity (trinary)	Non-required	0.4623	46.23%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8209	82.09%
Skin irritation	-	0.8463	84.63%
Skin corrosion	-	0.9775	97.75%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7754	77.54%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.6953	69.53%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8351	83.51%
Acute Oral Toxicity (c)	III	0.6419	64.19%
Estrogen receptor binding	+	0.8064	80.64%
Androgen receptor binding	+	0.6711	67.11%
Thyroid receptor binding	+	0.6454	64.54%
Glucocorticoid receptor binding	+	0.7140	71.40%
Aromatase binding	-	0.5533	55.33%
PPAR gamma	+	0.6518	65.18%
Honey bee toxicity	-	0.8276	82.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9806	98.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	616 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.80%	91.11%
CHEMBL4302	P08183	P-glycoprotein 1	90.81%	92.98%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.58%	97.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.84%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.71%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.80%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.25%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.26%	94.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.05%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.06%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.03%	89.62%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.84%	94.03%

Plants that contains it

• Achillea cretica
• Achillea holosericea
• Artemisia absinthium
• Artemisia arborescens
• Artemisia argentea
• Aspidosperma excelsum
• Chelonanthus albus
• Colocasia antiquorum
• Corymbia citriodora
• Eriosema chinense
• Laurelia novae-zelandiae
• Liriodendron tulipifera
• Magnolia biondii
• Magnolia denudata
• Magnolia kobus
• Ocotea heterochroma
• Peperomia obtusifolia
• Peperomia vulcanica
• Piper macropiper
• Tinospora sinensis
• Virola elongata
• Virola peruviana

Cross-Links

• PubChem: 99091
• NPASS: NPC328682
• ChEMBL: CHEMBL1412125
• LOTUS: LTS0132866
• wikiData: Q105032715