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

Details

• Internal ID: b2b9b003-3603-429a-abe6-4dc87754e77a
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (2R,3R,4R)-4-[(1R,2S)-3-[(2S,3R,4S,5S)-2-[(2R)-2-carboxy-2-hydroxyethyl]-4,5-dihydroxyoxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-2-[(1S)-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)CC(C(=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[C@H](C(=O)O)O)OC(=O)C2=CC3=CC(=C(C=C3[C@H]([C@@H]2C(=O)O[C@@H]4C=C(O[C@@H]([C@@H]4OC(=O)/C=C/C5=CC(=C(C=C5)O)O)[C@H](CO)O)C(=O)O)C6=CC(=C(C=C6)O)O)O)O)O)O
• InChI: InChI=1S/C43H42O23/c44-14-28(52)37-39(65-33(54)6-2-16-1-4-21(45)23(47)7-16)31(13-32(63-37)41(58)59)64-43(61)35-20(42(60)66-38-30(12-27(51)40(56)57)62-15-29(53)36(38)55)8-18-10-25(49)26(50)11-19(18)34(35)17-3-5-22(46)24(48)9-17/h1-11,13,27-31,34-39,44-53,55H,12,14-15H2,(H,56,57)(H,58,59)/b6-2+/t27-,28+,29+,30+,31-,34-,35-,36+,37-,38+,39-/m1/s1
• InChI Key: DAOFETOHYLHCHF-MTYGPQIHSA-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: 0.00
• 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	+	0.7986	79.86%
Caco-2	-	0.8829	88.29%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6947	69.47%
OATP2B1 inhibitior	-	0.7115	71.15%
OATP1B1 inhibitior	+	0.8350	83.50%
OATP1B3 inhibitior	+	0.9653	96.53%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8259	82.59%
P-glycoprotein inhibitior	+	0.7170	71.70%
P-glycoprotein substrate	+	0.6957	69.57%
CYP3A4 substrate	+	0.7155	71.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8648	86.48%
CYP3A4 inhibition	-	0.8768	87.68%
CYP2C9 inhibition	-	0.7686	76.86%
CYP2C19 inhibition	-	0.6989	69.89%
CYP2D6 inhibition	-	0.8736	87.36%
CYP1A2 inhibition	-	0.7722	77.22%
CYP2C8 inhibition	+	0.8090	80.90%
CYP inhibitory promiscuity	-	0.8305	83.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6599	65.99%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8974	89.74%
Skin irritation	-	0.8159	81.59%
Skin corrosion	-	0.9523	95.23%
Ames mutagenesis	-	0.5957	59.57%
Human Ether-a-go-go-Related Gene inhibition	+	0.7043	70.43%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8347	83.47%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9643	96.43%
Acute Oral Toxicity (c)	III	0.4177	41.77%
Estrogen receptor binding	+	0.7535	75.35%
Androgen receptor binding	+	0.7135	71.35%
Thyroid receptor binding	+	0.5248	52.48%
Glucocorticoid receptor binding	-	0.5148	51.48%
Aromatase binding	+	0.5226	52.26%
PPAR gamma	+	0.7362	73.62%
Honey bee toxicity	-	0.6349	63.49%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9741	97.41%

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	99.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.13%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.08%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	95.29%	96.38%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.15%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	94.84%	90.17%
CHEMBL3194	P02766	Transthyretin	94.77%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.14%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.82%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.78%	99.15%
CHEMBL226	P30542	Adenosine A1 receptor	92.59%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.13%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.69%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.03%	99.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	89.10%	83.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.06%	91.49%
CHEMBL2581	P07339	Cathepsin D	88.70%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	88.62%	83.82%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	88.61%	96.37%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.57%	95.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.06%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	87.64%	91.71%
CHEMBL340	P08684	Cytochrome P450 3A4	87.13%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.97%	97.28%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.98%	100.00%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	83.51%	90.24%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	83.36%	98.75%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.15%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.70%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.31%	97.33%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.79%	89.62%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.24%	97.53%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 162979435
• LOTUS: LTS0099319
• wikiData: Q104973767