(1S,4R,5S,17R,19S,20R)-8,20-dihydroxy-19-(hydroxymethyl)-5-(4-hydroxyphenyl)-7,9-dimethoxy-19-[(2R,3R,4S,5S,6R)-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: 32b07a02-73fd-4b1f-970a-3c54cbc3809e
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (1S,4R,5S,17R,19S,20R)-8,20-dihydroxy-19-(hydroxymethyl)-5-(4-hydroxyphenyl)-7,9-dimethoxy-19-[(2R,3R,4S,5S,6R)-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(=C2C(C3C(=CC2=C1)C(=O)OCC4C(C(C(O4)(CO)OC5C(C(C(C(O5)CO)O)O)O)OC3=O)O)C6=CC=C(C=C6)O)OC)O
• SMILES (Isomeric): COC1=C(C(=C2[C@@H]([C@@H]3C(=CC2=C1)C(=O)OC[C@@H]4[C@H]([C@@H]([C@](O4)(CO)O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC3=O)O)C6=CC=C(C=C6)O)OC)O
• InChI: InChI=1S/C32H36O17/c1-43-16-8-13-7-15-21(19(12-3-5-14(35)6-4-12)20(13)27(44-2)23(16)37)30(42)47-28-24(38)18(10-45-29(15)41)48-32(28,11-34)49-31-26(40)25(39)22(36)17(9-33)46-31/h3-8,17-19,21-22,24-26,28,31,33-40H,9-11H2,1-2H3/t17-,18-,19+,21+,22-,24-,25+,26-,28+,31-,32+/m1/s1
• InChI Key: QOIOXLKARYNOJQ-DGUITQJSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₆O₁₇
• Molecular Weight: 692.60 g/mol
• Exact Mass: 692.19524968 g/mol
• Topological Polar Surface Area (TPSA): 261.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -2.01
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7061	70.61%
Caco-2	-	0.9022	90.22%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7797	77.97%
OATP2B1 inhibitior	-	0.7296	72.96%
OATP1B1 inhibitior	+	0.8164	81.64%
OATP1B3 inhibitior	+	0.9559	95.59%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8414	84.14%
P-glycoprotein inhibitior	-	0.4598	45.98%
P-glycoprotein substrate	+	0.6064	60.64%
CYP3A4 substrate	+	0.7026	70.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8678	86.78%
CYP3A4 inhibition	-	0.8222	82.22%
CYP2C9 inhibition	-	0.7092	70.92%
CYP2C19 inhibition	-	0.6864	68.64%
CYP2D6 inhibition	-	0.9065	90.65%
CYP1A2 inhibition	-	0.8461	84.61%
CYP2C8 inhibition	+	0.7050	70.50%
CYP inhibitory promiscuity	-	0.6086	60.86%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6050	60.50%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9215	92.15%
Skin irritation	-	0.7982	79.82%
Skin corrosion	-	0.9413	94.13%
Ames mutagenesis	-	0.5328	53.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7094	70.94%
Micronuclear	+	0.5974	59.74%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8176	81.76%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8422	84.22%
Acute Oral Toxicity (c)	III	0.4033	40.33%
Estrogen receptor binding	+	0.8800	88.00%
Androgen receptor binding	+	0.6990	69.90%
Thyroid receptor binding	+	0.5529	55.29%
Glucocorticoid receptor binding	+	0.6803	68.03%
Aromatase binding	+	0.5943	59.43%
PPAR gamma	+	0.7273	72.73%
Honey bee toxicity	-	0.6382	63.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6049	60.49%
Fish aquatic toxicity	+	0.9727	97.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.85%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.26%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	96.48%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.80%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.46%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.18%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.50%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.41%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.06%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	91.64%	95.89%
CHEMBL2581	P07339	Cathepsin D	90.80%	98.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	88.88%	97.33%
CHEMBL3401	O75469	Pregnane X receptor	88.77%	94.73%
CHEMBL2535	P11166	Glucose transporter	88.59%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.80%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.33%	96.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.92%	92.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.71%	96.61%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.27%	100.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.22%	86.92%
CHEMBL3524	P56524	Histone deacetylase 4	80.82%	92.97%
CHEMBL4208	P20618	Proteasome component C5	80.78%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.38%	89.62%

Plants that contains it

• Eritrichium pauciflorum

Cross-Links

• PubChem: 11520418
• LOTUS: LTS0157516
• wikiData: Q105224910