[(2R,3S,4S,5R,6R)-6-[[(1S,4S,5R,17R,19R,20R)-8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-6,8,10,12-tetraen-19-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: 775a83fb-3b05-4119-956c-6af8c13582a4
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(1S,4S,5R,17R,19R,20R)-8,20-dihydroxy-5-(4-hydroxy-3-methoxyphenyl)-19-(hydroxymethyl)-9-methoxy-3,14-dioxo-2,15,18-trioxatetracyclo[15.2.1.04,13.06,11]icosa-6,8,10,12-tetraen-19-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C3C(C(O2)COC(=O)C4=CC5=CC(=C(C=C5C(C4C(=O)O3)C6=CC(=C(C=C6)O)OC)O)OC)O)CO)O)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@@]2([C@@H]3[C@@H]([C@H](O2)COC(=O)C4=CC5=CC(=C(C=C5[C@H]([C@@H]4C(=O)O3)C6=CC(=C(C=C6)O)OC)O)OC)O)CO)O)O)O
• InChI: InChI=1S/C34H38O18/c1-13(36)47-10-22-26(39)28(41)29(42)33(49-22)52-34(12-35)30-27(40)23(51-34)11-48-31(43)17-6-15-8-21(46-3)19(38)9-16(15)24(25(17)32(44)50-30)14-4-5-18(37)20(7-14)45-2/h4-9,22-30,33,35,37-42H,10-12H2,1-3H3/t22-,23-,24-,25-,26-,27-,28+,29-,30+,33-,34-/m1/s1
• InChI Key: XOMTWRCRDIWSSU-KKWQDSCFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₃₈O₁₈
• Molecular Weight: 734.70 g/mol
• Exact Mass: 734.20581436 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: -1.20
• Atomic LogP (AlogP): -1.44
• H-Bond Acceptor: 18
• H-Bond Donor: 7
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8050	80.50%
Caco-2	-	0.8862	88.62%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7365	73.65%
OATP2B1 inhibitior	-	0.7209	72.09%
OATP1B1 inhibitior	+	0.8434	84.34%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7958	79.58%
P-glycoprotein inhibitior	+	0.6459	64.59%
P-glycoprotein substrate	+	0.6181	61.81%
CYP3A4 substrate	+	0.7047	70.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.8885	88.85%
CYP2C9 inhibition	-	0.7832	78.32%
CYP2C19 inhibition	-	0.7695	76.95%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.8417	84.17%
CYP2C8 inhibition	+	0.6910	69.10%
CYP inhibitory promiscuity	-	0.6977	69.77%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6371	63.71%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9200	92.00%
Skin irritation	-	0.7813	78.13%
Skin corrosion	-	0.9407	94.07%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6729	67.29%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8426	84.26%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7066	70.66%
Acute Oral Toxicity (c)	I	0.3947	39.47%
Estrogen receptor binding	+	0.8781	87.81%
Androgen receptor binding	+	0.6951	69.51%
Thyroid receptor binding	+	0.5288	52.88%
Glucocorticoid receptor binding	+	0.7329	73.29%
Aromatase binding	+	0.6316	63.16%
PPAR gamma	+	0.7456	74.56%
Honey bee toxicity	-	0.7082	70.82%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9847	98.47%

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	99.96%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.77%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.03%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.30%	91.49%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.96%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.63%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.25%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.29%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.44%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.07%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.26%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.00%	86.33%
CHEMBL2535	P11166	Glucose transporter	90.19%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.59%	94.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.11%	97.25%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.06%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	87.48%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.23%	99.17%
CHEMBL340	P08684	Cytochrome P450 3A4	85.07%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.94%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.07%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.22%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.65%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.46%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.24%	85.31%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.98%	95.83%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.95%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.74%	89.62%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.36%	100.00%
CHEMBL4208	P20618	Proteasome component C5	80.02%	90.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.00%	82.50%

Plants that contains it

• Trigonotis peduncularis

Cross-Links

• PubChem: 162986864
• LOTUS: LTS0205260
• wikiData: Q105337815