5-[[(3R,4R,5S)-5-methoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl]methyl]-1,3-benzodioxole

Details

• Internal ID: 3cea6440-3403-429a-a22a-e41e17286477
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans
• IUPAC Name: 5-[[(3R,4R,5S)-5-methoxy-4-[(3,4,5-trimethoxyphenyl)methyl]oxolan-3-yl]methyl]-1,3-benzodioxole
• SMILES (Canonical): COC1C(C(CO1)CC2=CC3=C(C=C2)OCO3)CC4=CC(=C(C(=C4)OC)OC)OC
• SMILES (Isomeric): CO[C@@H]1[C@@H]([C@H](CO1)CC2=CC3=C(C=C2)OCO3)CC4=CC(=C(C(=C4)OC)OC)OC
• InChI: InChI=1S/C23H28O7/c1-24-20-10-15(11-21(25-2)22(20)26-3)8-17-16(12-28-23(17)27-4)7-14-5-6-18-19(9-14)30-13-29-18/h5-6,9-11,16-17,23H,7-8,12-13H2,1-4H3/t16-,17+,23-/m0/s1
• InChI Key: LMMVWMMBIFKQPI-MFEFFIJZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₇
• Molecular Weight: 416.50 g/mol
• Exact Mass: 416.18350323 g/mol
• Topological Polar Surface Area (TPSA): 64.60 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.46
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9775	97.75%
Caco-2	+	0.8407	84.07%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6823	68.23%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9286	92.86%
OATP1B3 inhibitior	+	0.9608	96.08%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9618	96.18%
P-glycoprotein inhibitior	+	0.8314	83.14%
P-glycoprotein substrate	-	0.6998	69.98%
CYP3A4 substrate	+	0.5895	58.95%
CYP2C9 substrate	-	0.8104	81.04%
CYP2D6 substrate	+	0.4123	41.23%
CYP3A4 inhibition	+	0.9084	90.84%
CYP2C9 inhibition	+	0.7707	77.07%
CYP2C19 inhibition	+	0.9313	93.13%
CYP2D6 inhibition	-	0.5224	52.24%
CYP1A2 inhibition	+	0.6969	69.69%
CYP2C8 inhibition	+	0.6064	60.64%
CYP inhibitory promiscuity	+	0.9387	93.87%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9308	93.08%
Carcinogenicity (trinary)	Non-required	0.4383	43.83%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.9006	90.06%
Skin irritation	-	0.8412	84.12%
Skin corrosion	-	0.9694	96.94%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9164	91.64%
Micronuclear	+	0.5800	58.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6320	63.20%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.8370	83.70%
Acute Oral Toxicity (c)	III	0.5819	58.19%
Estrogen receptor binding	+	0.8801	88.01%
Androgen receptor binding	+	0.6001	60.01%
Thyroid receptor binding	+	0.6778	67.78%
Glucocorticoid receptor binding	+	0.7936	79.36%
Aromatase binding	+	0.5413	54.13%
PPAR gamma	+	0.6920	69.20%
Honey bee toxicity	-	0.7442	74.42%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9858	98.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.46%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	97.34%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.43%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.55%	92.62%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.67%	96.77%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.92%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.18%	98.95%
CHEMBL261	P00915	Carbonic anhydrase I	89.66%	96.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.08%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.21%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.06%	86.33%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.57%	80.96%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	86.86%	85.49%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.83%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.59%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.39%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.68%	97.09%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.20%	89.44%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.02%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.93%	94.00%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	82.86%	91.43%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.34%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.10%	93.99%

Plants that contains it

• Lychnophora ericoides

Cross-Links

• PubChem: 162856850
• LOTUS: LTS0025175
• wikiData: Q105154057