(2R,3R,4R)-4-[(1R)-3-[(2S,3R,4S,5S)-2-(2-carboxy-1-hydroxyethyl)-4,5-dihydroxyoxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-2-(1,2-dihydroxyethyl)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid

Details

• Internal ID: c55b8907-3cb0-44be-aa87-c2fdf07c2900
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (2R,3R,4R)-4-[(1R)-3-[(2S,3R,4S,5S)-2-(2-carboxy-1-hydroxyethyl)-4,5-dihydroxyoxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-2-(1,2-dihydroxyethyl)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydro-2H-pyran-6-carboxylic acid
• SMILES (Canonical): C1C(C(C(C(O1)C(CC(=O)O)O)OC(=O)C2=CC3=CC(=C(C=C3C(C2C(=O)OC4C=C(OC(C4OC(=O)C=CC5=CC(=C(C=C5)O)O)C(CO)O)C(=O)O)C6=CC(=C(C=C6)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H]([C@H]([C@@H](O1)C(CC(=O)O)O)OC(=O)C2=CC3=CC(=C(C=C3[C@H](C2C(=O)O[C@@H]4C=C(O[C@@H]([C@@H]4OC(=O)/C=C/C5=CC(=C(C=C5)O)O)C(CO)O)C(=O)O)C6=CC(=C(C=C6)O)O)O)O)O)O
• InChI: InChI=1S/C43H42O23/c44-14-28(52)38-39(65-33(56)6-2-16-1-4-21(45)23(47)7-16)30(13-31(63-38)41(58)59)64-43(61)35-20(42(60)66-40-36(57)29(53)15-62-37(40)27(51)12-32(54)55)8-18-10-25(49)26(50)11-19(18)34(35)17-3-5-22(46)24(48)9-17/h1-11,13,27-30,34-40,44-53,57H,12,14-15H2,(H,54,55)(H,58,59)/b6-2+/t27?,28?,29-,30+,34+,35?,36-,37-,38+,39+,40+/m0/s1
• InChI Key: VMGGBASUKFHQIY-NTRNNTEPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₂O₂₃
• Molecular Weight: 926.80 g/mol
• Exact Mass: 926.21168758 g/mol
• Topological Polar Surface Area (TPSA): 395.00 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): -0.81
• H-Bond Acceptor: 21
• 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	+	0.6216	62.16%
Caco-2	-	0.8834	88.34%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5440	54.40%
OATP2B1 inhibitior	-	0.7096	70.96%
OATP1B1 inhibitior	+	0.8455	84.55%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7770	77.70%
P-glycoprotein inhibitior	+	0.7133	71.33%
P-glycoprotein substrate	+	0.7033	70.33%
CYP3A4 substrate	+	0.7155	71.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8669	86.69%
CYP3A4 inhibition	-	0.9051	90.51%
CYP2C9 inhibition	-	0.8587	85.87%
CYP2C19 inhibition	-	0.8157	81.57%
CYP2D6 inhibition	-	0.8858	88.58%
CYP1A2 inhibition	-	0.8571	85.71%
CYP2C8 inhibition	+	0.8099	80.99%
CYP inhibitory promiscuity	-	0.8590	85.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7344	73.44%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.8962	89.62%
Skin irritation	-	0.8189	81.89%
Skin corrosion	-	0.9562	95.62%
Ames mutagenesis	-	0.5087	50.87%
Human Ether-a-go-go-Related Gene inhibition	+	0.7365	73.65%
Micronuclear	+	0.5374	53.74%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.8395	83.95%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9586	95.86%
Acute Oral Toxicity (c)	III	0.4142	41.42%
Estrogen receptor binding	+	0.7402	74.02%
Androgen receptor binding	+	0.6972	69.72%
Thyroid receptor binding	+	0.5290	52.90%
Glucocorticoid receptor binding	-	0.5333	53.33%
Aromatase binding	-	0.4839	48.39%
PPAR gamma	+	0.7270	72.70%
Honey bee toxicity	-	0.6326	63.26%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9588	95.88%

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	99.92%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.04%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.87%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.22%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.10%	99.15%
CHEMBL4040	P28482	MAP kinase ERK2	94.78%	83.82%
CHEMBL3194	P02766	Transthyretin	94.58%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.48%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	94.35%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.06%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.02%	86.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.04%	96.38%
CHEMBL226	P30542	Adenosine A1 receptor	89.81%	95.93%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.64%	99.17%
CHEMBL2581	P07339	Cathepsin D	88.63%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.62%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.00%	95.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	87.92%	96.37%
CHEMBL340	P08684	Cytochrome P450 3A4	87.10%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.66%	97.28%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.13%	98.75%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	83.67%	83.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.32%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	82.39%	95.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.29%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.58%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.09%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	80.20%	91.49%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 101231538
• LOTUS: LTS0105546
• wikiData: Q105288971