(2R)-2-[(1R)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid

Details

• Internal ID: 94c8a49e-9d35-44af-8346-41afc98f116f
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R)-2-[(1R)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C2C(C3=CC(=C(C=C3C=C2C(=O)OC(CC4=CC(=C(C=C4)O)O)C(=O)O)O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC(=C(C=C6)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)C2[C@@H](C3=CC(=C(C=C3C=C2C(=O)O[C@H](CC4=CC(=C(C=C4)O)O)C(=O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C6=CC(=C(C=C6)O)O)O)O
• InChI: InChI=1S/C42H40O21/c43-15-32-35(51)36(52)37(53)42(63-32)62-29-14-20-19(13-28(29)50)11-21(40(58)60-30(38(54)55)9-16-1-4-22(44)25(47)7-16)34(33(20)18-3-6-24(46)27(49)12-18)41(59)61-31(39(56)57)10-17-2-5-23(45)26(48)8-17/h1-8,11-14,30-37,42-53H,9-10,15H2,(H,54,55)(H,56,57)/t30-,31-,32-,33-,34?,35-,36+,37-,42-/m1/s1
• InChI Key: HRBXHLVQWNWQGM-ZQCHAWBISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₄₀O₂₁
• Molecular Weight: 880.80 g/mol
• Exact Mass: 880.20620828 g/mol
• Topological Polar Surface Area (TPSA): 368.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 0.43
• H-Bond Acceptor: 19
• H-Bond Donor: 13
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6912	69.12%
Caco-2	-	0.8953	89.53%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.5598	55.98%
OATP2B1 inhibitior	-	0.7104	71.04%
OATP1B1 inhibitior	+	0.8659	86.59%
OATP1B3 inhibitior	+	0.9607	96.07%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7801	78.01%
P-glycoprotein inhibitior	+	0.6979	69.79%
P-glycoprotein substrate	-	0.6397	63.97%
CYP3A4 substrate	+	0.6625	66.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8693	86.93%
CYP3A4 inhibition	-	0.9119	91.19%
CYP2C9 inhibition	-	0.7022	70.22%
CYP2C19 inhibition	-	0.7551	75.51%
CYP2D6 inhibition	-	0.9093	90.93%
CYP1A2 inhibition	-	0.7788	77.88%
CYP2C8 inhibition	+	0.7376	73.76%
CYP inhibitory promiscuity	-	0.5785	57.85%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7313	73.13%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9000	90.00%
Skin irritation	-	0.8032	80.32%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7640	76.40%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8415	84.15%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	-	0.7702	77.02%
Acute Oral Toxicity (c)	III	0.3674	36.74%
Estrogen receptor binding	+	0.7868	78.68%
Androgen receptor binding	+	0.6879	68.79%
Thyroid receptor binding	+	0.5181	51.81%
Glucocorticoid receptor binding	-	0.5508	55.08%
Aromatase binding	-	0.5137	51.37%
PPAR gamma	+	0.7170	71.70%
Honey bee toxicity	-	0.6213	62.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5799	57.99%
Fish aquatic toxicity	+	0.9673	96.73%

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	99.23%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.11%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.48%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	95.51%	91.49%
CHEMBL4040	P28482	MAP kinase ERK2	95.20%	83.82%
CHEMBL2581	P07339	Cathepsin D	93.31%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.72%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.77%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.47%	86.92%
CHEMBL3194	P02766	Transthyretin	88.32%	90.71%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.81%	95.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	87.54%	89.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.22%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.03%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.29%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.19%	94.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.70%	89.44%

Plants that contains it

• Arnebia euchroma

Cross-Links

• PubChem: 44575680
• LOTUS: LTS0064146
• wikiData: Q105032567