8,20-Dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-7,9-dimethoxy-19-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-6,8,10,12-tetraene-3,14-dione

Details

• Internal ID: 5258a2a0-454d-44ff-9f3b-0cf371d822a3
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-7,9-dimethoxy-19-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-6,8,10,12-tetraene-3,14-dione
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3C(=CC4=CC(=C(C(=C24)OC)O)OC)C(=O)OCC5C(C(C(O5)(CO)OC6C(C(C(C(O6)CO)O)O)O)OC3=O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2C3C(=CC4=CC(=C(C(=C24)OC)O)OC)C(=O)OCC5C(C(C(O5)(CO)OC6C(C(C(C(O6)CO)O)O)O)OC3=O)O)O
• InChI: InChI=1S/C33H38O18/c1-44-16-7-12(4-5-15(16)36)20-21-13(8-17(45-2)24(38)28(21)46-3)6-14-22(20)31(43)49-29-25(39)19(10-47-30(14)42)50-33(29,11-35)51-32-27(41)26(40)23(37)18(9-34)48-32/h4-8,18-20,22-23,25-27,29,32,34-41H,9-11H2,1-3H3
• InChI Key: VZLIQNLXUYMNAA-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₃₈O₁₈
• Molecular Weight: 722.60 g/mol
• Exact Mass: 722.20581436 g/mol
• Topological Polar Surface Area (TPSA): 270.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -2.00
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7158	71.58%
Caco-2	-	0.8929	89.29%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7569	75.69%
OATP2B1 inhibitior	-	0.7261	72.61%
OATP1B1 inhibitior	+	0.8390	83.90%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8896	88.96%
P-glycoprotein inhibitior	+	0.5925	59.25%
P-glycoprotein substrate	+	0.5753	57.53%
CYP3A4 substrate	+	0.6959	69.59%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8678	86.78%
CYP3A4 inhibition	-	0.8484	84.84%
CYP2C9 inhibition	-	0.7317	73.17%
CYP2C19 inhibition	-	0.7270	72.70%
CYP2D6 inhibition	-	0.9246	92.46%
CYP1A2 inhibition	-	0.8588	85.88%
CYP2C8 inhibition	+	0.6804	68.04%
CYP inhibitory promiscuity	-	0.6405	64.05%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5823	58.23%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.9165	91.65%
Skin irritation	-	0.7937	79.37%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.5454	54.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6632	66.32%
Micronuclear	+	0.5774	57.74%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8298	82.98%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.8996	89.96%
Acute Oral Toxicity (c)	III	0.3868	38.68%
Estrogen receptor binding	+	0.8674	86.74%
Androgen receptor binding	+	0.6886	68.86%
Thyroid receptor binding	+	0.5549	55.49%
Glucocorticoid receptor binding	+	0.7087	70.87%
Aromatase binding	+	0.6225	62.25%
PPAR gamma	+	0.7340	73.40%
Honey bee toxicity	-	0.6654	66.54%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9730	97.30%

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	99.89%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.87%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	98.37%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.34%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.88%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.37%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.78%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.82%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.80%	95.89%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.25%	99.15%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.86%	96.61%
CHEMBL2581	P07339	Cathepsin D	89.84%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.36%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	88.66%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.05%	92.62%
CHEMBL2535	P11166	Glucose transporter	87.64%	98.75%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.46%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.66%	99.17%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.68%	100.00%
CHEMBL4208	P20618	Proteasome component C5	82.85%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.25%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.19%	89.62%

Plants that contains it

• Trigonotis peduncularis

Cross-Links

• PubChem: 162979884
• LOTUS: LTS0150230
• wikiData: Q105299831