4-[(3S,3aR,6S,6aR)-6-(4-methyl-1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol

Details

• Internal ID: 5b4310a3-b2bd-4cdd-a507-1fe43315d63c
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans
• IUPAC Name: 4-[(3S,3aR,6S,6aR)-6-(4-methyl-1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
• SMILES (Canonical): CC1=C(C=CC2=C1OCO2)C3C4COC(C4CO3)C5=CC(=C(C=C5)O)OC
• SMILES (Isomeric): CC1=C(C=CC2=C1OCO2)[C@@H]3[C@H]4CO[C@@H]([C@H]4CO3)C5=CC(=C(C=C5)O)OC
• InChI: InChI=1S/C21H22O6/c1-11-13(4-6-17-19(11)27-10-26-17)21-15-9-24-20(14(15)8-25-21)12-3-5-16(22)18(7-12)23-2/h3-7,14-15,20-22H,8-10H2,1-2H3/t14-,15-,20+,21+/m0/s1
• InChI Key: OFCHTGCBFRTISG-VUEDXXQZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14163842 g/mol
• Topological Polar Surface Area (TPSA): 66.40 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9792	97.92%
Caco-2	+	0.6828	68.28%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7671	76.71%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9114	91.14%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.4744	47.44%
P-glycoprotein inhibitior	+	0.6666	66.66%
P-glycoprotein substrate	-	0.8533	85.33%
CYP3A4 substrate	+	0.5908	59.08%
CYP2C9 substrate	-	0.7765	77.65%
CYP2D6 substrate	-	0.6872	68.72%
CYP3A4 inhibition	+	0.9194	91.94%
CYP2C9 inhibition	+	0.8304	83.04%
CYP2C19 inhibition	+	0.8700	87.00%
CYP2D6 inhibition	-	0.5267	52.67%
CYP1A2 inhibition	+	0.5230	52.30%
CYP2C8 inhibition	+	0.6922	69.22%
CYP inhibitory promiscuity	+	0.8981	89.81%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9108	91.08%
Carcinogenicity (trinary)	Non-required	0.4397	43.97%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.8338	83.38%
Skin irritation	-	0.8171	81.71%
Skin corrosion	-	0.9651	96.51%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7932	79.32%
Micronuclear	+	0.7000	70.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.7144	71.44%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7676	76.76%
Acute Oral Toxicity (c)	III	0.5282	52.82%
Estrogen receptor binding	+	0.8671	86.71%
Androgen receptor binding	+	0.7685	76.85%
Thyroid receptor binding	+	0.6876	68.76%
Glucocorticoid receptor binding	+	0.7122	71.22%
Aromatase binding	-	0.6326	63.26%
PPAR gamma	+	0.5310	53.10%
Honey bee toxicity	-	0.8474	84.74%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9839	98.39%

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	97.93%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.48%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.66%	96.09%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	93.09%	89.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.51%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.21%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.99%	86.33%
CHEMBL2535	P11166	Glucose transporter	90.74%	98.75%
CHEMBL2581	P07339	Cathepsin D	89.90%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.78%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.33%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.10%	85.14%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	87.71%	82.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.69%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	86.01%	91.49%
CHEMBL3438	Q05513	Protein kinase C zeta	83.58%	88.48%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.24%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.83%	94.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	81.12%	85.49%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.80%	93.40%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.80%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.17%	100.00%

Plants that contains it

• Leucophyllum ambiguum

Cross-Links

• PubChem: 44559453
• LOTUS: LTS0200130
• wikiData: Q103815912