Pinoresinol-4'-O-[3',6'-O-(E)-diferuloyl]-beta-D-glucopyranoside

Details

• Internal ID: 110ec63f-cb22-4b06-a37b-00114c35d20b
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: [(2R,3R,4S,5R,6S)-6-[4-[(3R,3aS,6R,6aS)-3-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-3,5-dihydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3=C(C=C(C=C3)C4C5COC(C5CO4)C6=CC(=C(C=C6)O)OC)OC)O)OC(=O)C=CC7=CC(=C(C=C7)O)OC)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(C=C(C=C3)[C@H]4[C@@H]5CO[C@H]([C@@H]5CO4)C6=CC(=C(C=C6)O)OC)OC)O)OC(=O)/C=C/C7=CC(=C(C=C7)O)OC)O)O
• InChI: InChI=1S/C46H48O17/c1-54-34-17-24(5-11-30(34)47)7-15-39(50)58-23-38-41(52)45(63-40(51)16-8-25-6-12-31(48)35(18-25)55-2)42(53)46(62-38)61-33-14-10-27(20-37(33)57-4)44-29-22-59-43(28(29)21-60-44)26-9-13-32(49)36(19-26)56-3/h5-20,28-29,38,41-49,52-53H,21-23H2,1-4H3/b15-7+,16-8+/t28-,29-,38-,41-,42-,43+,44+,45+,46-/m1/s1
• InChI Key: LVCYOGTWEKMMSO-PMGFHEBOSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₄₈O₁₇
• Molecular Weight: 872.90 g/mol
• Exact Mass: 872.28915006 g/mol
• Topological Polar Surface Area (TPSA): 228.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.62
• H-Bond Acceptor: 17
• H-Bond Donor: 5
• Rotatable Bonds: 15

Synonyms

• PINORESINOL-4'-O-[3',6'-O-(E)-DIFERULOYL]-BETA-D-GLUCOPYRANOSIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9142	91.42%
Caco-2	-	0.8651	86.51%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7494	74.94%
OATP2B1 inhibitior	+	0.5608	56.08%
OATP1B1 inhibitior	+	0.8589	85.89%
OATP1B3 inhibitior	+	0.9019	90.19%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8654	86.54%
P-glycoprotein inhibitior	+	0.7617	76.17%
P-glycoprotein substrate	-	0.6422	64.22%
CYP3A4 substrate	+	0.6655	66.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8599	85.99%
CYP3A4 inhibition	-	0.7284	72.84%
CYP2C9 inhibition	-	0.6868	68.68%
CYP2C19 inhibition	-	0.6850	68.50%
CYP2D6 inhibition	-	0.9347	93.47%
CYP1A2 inhibition	-	0.8930	89.30%
CYP2C8 inhibition	+	0.7530	75.30%
CYP inhibitory promiscuity	+	0.5475	54.75%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5647	56.47%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9055	90.55%
Skin irritation	-	0.8597	85.97%
Skin corrosion	-	0.9588	95.88%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7650	76.50%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.7893	78.93%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9799	97.99%
Acute Oral Toxicity (c)	III	0.5289	52.89%
Estrogen receptor binding	+	0.7771	77.71%
Androgen receptor binding	+	0.7238	72.38%
Thyroid receptor binding	+	0.5980	59.80%
Glucocorticoid receptor binding	+	0.7136	71.36%
Aromatase binding	+	0.5530	55.30%
PPAR gamma	+	0.7450	74.50%
Honey bee toxicity	-	0.7964	79.64%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9867	98.67%

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	99.33%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.94%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	98.60%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.42%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.04%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.61%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.55%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.60%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.71%	99.17%
CHEMBL3194	P02766	Transthyretin	87.86%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.25%	89.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.82%	92.94%
CHEMBL4208	P20618	Proteasome component C5	85.84%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.35%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.22%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.03%	92.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.90%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	83.47%	94.73%
CHEMBL5255	O00206	Toll-like receptor 4	83.14%	92.50%
CHEMBL5028	O14672	ADAM10	83.06%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.59%	94.45%

Plants that contains it

• Brucea javanica

Cross-Links

• PubChem: 17755815
• LOTUS: LTS0191987
• wikiData: Q105157792