1alpha-(1,3-Benzodioxole-5-yl)-3aalpha-hydroxy-4alpha-(3-methoxy-4-hydroxyphenyl)-3aalpha,4,6,6aalpha-tetrahydro-1H,3H-furo[3,4-c]furan

Details

• Internal ID: 5aac35ce-a0d4-45ae-8e16-ff96cd142c51
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: (3S,3aR,6R,6aS)-6-(1,3-benzodioxol-5-yl)-3-(4-hydroxy-3-methoxyphenyl)-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3a-ol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3(COC(C3CO2)C4=CC5=C(C=C4)OCO5)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@@]3(CO[C@H]([C@@H]3CO2)C4=CC5=C(C=C4)OCO5)O)O
• InChI: InChI=1S/C20H20O7/c1-23-16-7-12(2-4-14(16)21)19-20(22)9-25-18(13(20)8-24-19)11-3-5-15-17(6-11)27-10-26-15/h2-7,13,18-19,21-22H,8-10H2,1H3/t13-,18-,19-,20-/m0/s1
• InChI Key: WFZIOQOKIOIJHN-KJYZGMDISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.40 g/mol
• Exact Mass: 372.12090297 g/mol
• Topological Polar Surface Area (TPSA): 86.60 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9697	96.97%
Caco-2	-	0.5532	55.32%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7734	77.34%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9153	91.53%
OATP1B3 inhibitior	+	0.9549	95.49%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6859	68.59%
P-glycoprotein inhibitior	+	0.5790	57.90%
P-glycoprotein substrate	-	0.8426	84.26%
CYP3A4 substrate	+	0.5892	58.92%
CYP2C9 substrate	-	0.8042	80.42%
CYP2D6 substrate	-	0.7254	72.54%
CYP3A4 inhibition	+	0.5210	52.10%
CYP2C9 inhibition	-	0.5757	57.57%
CYP2C19 inhibition	+	0.5394	53.94%
CYP2D6 inhibition	-	0.7822	78.22%
CYP1A2 inhibition	-	0.8459	84.59%
CYP2C8 inhibition	+	0.5559	55.59%
CYP inhibitory promiscuity	-	0.6075	60.75%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.3627	36.27%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8623	86.23%
Skin irritation	-	0.8088	80.88%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4273	42.73%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8483	84.83%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6910	69.10%
Acute Oral Toxicity (c)	III	0.5700	57.00%
Estrogen receptor binding	+	0.9022	90.22%
Androgen receptor binding	+	0.7280	72.80%
Thyroid receptor binding	+	0.7264	72.64%
Glucocorticoid receptor binding	+	0.6393	63.93%
Aromatase binding	-	0.5308	53.08%
PPAR gamma	+	0.7720	77.20%
Honey bee toxicity	-	0.8165	81.65%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9456	94.56%

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	99.68%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.17%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.51%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.56%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.13%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.89%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.48%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.78%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.92%	89.62%
CHEMBL3438	Q05513	Protein kinase C zeta	88.75%	88.48%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.37%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.04%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.03%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.96%	96.77%
CHEMBL4208	P20618	Proteasome component C5	85.67%	90.00%
CHEMBL2535	P11166	Glucose transporter	85.40%	98.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.98%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.39%	92.94%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.82%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.01%	100.00%
CHEMBL1951	P21397	Monoamine oxidase A	81.55%	91.49%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.92%	85.49%

Plants that contains it

• Handroanthus impetiginosus

Cross-Links

• PubChem: 102501953
• NPASS: NPC198353