(1R,2S)-5-[(5R,6S)-6-carboxy-7-[(2R,3R,4S,5R)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxycarbonyl-5-(3,4-dihydroxyphenyl)-2,3-dihydroxy-5,6-dihydronaphthalen-1-yl]-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid

Details

• Internal ID: 60d9659b-228b-452f-b817-bdfd68f024ca
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (1R,2S)-5-[(5R,6S)-6-carboxy-7-[(2R,3R,4S,5R)-2-(carboxymethyl)-4,5-dihydroxyoxan-3-yl]oxycarbonyl-5-(3,4-dihydroxyphenyl)-2,3-dihydroxy-5,6-dihydronaphthalen-1-yl]-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid
• SMILES (Canonical): C1C(C(C(C(O1)CC(=O)O)OC(=O)C2=CC3=C(C(=C(C=C3C(C2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)C5=C6C=C(C(C(C6=CC(=C5O)O)C7=CC(=C(C=C7)O)O)C(=O)O)C(=O)O)O)O
• SMILES (Isomeric): C1[C@H]([C@@H]([C@H]([C@H](O1)CC(=O)O)OC(=O)C2=CC3=C(C(=C(C=C3[C@H]([C@@H]2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)C5=C6C=C([C@H]([C@@H](C6=CC(=C5O)O)C7=CC(=C(C=C7)O)O)C(=O)O)C(=O)O)O)O
• InChI: InChI=1S/C43H36O21/c44-21-3-1-13(5-23(21)46)30-17-9-25(48)36(53)32(15(17)7-19(40(56)57)34(30)41(58)59)33-16-8-20(43(62)64-39-28(11-29(51)52)63-12-27(50)38(39)55)35(42(60)61)31(18(16)10-26(49)37(33)54)14-2-4-22(45)24(47)6-14/h1-10,27-28,30-31,34-35,38-39,44-50,53-55H,11-12H2,(H,51,52)(H,56,57)(H,58,59)(H,60,61)/t27-,28-,30-,31-,34-,35-,38+,39+/m1/s1
• InChI Key: NZVOYXMWNIGTLX-SJELJKPJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₃₆O₂₁
• Molecular Weight: 888.70 g/mol
• Exact Mass: 888.17490815 g/mol
• Topological Polar Surface Area (TPSA): 387.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.05
• H-Bond Acceptor: 17
• H-Bond Donor: 14
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8833	88.33%
Caco-2	-	0.8965	89.65%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7486	74.86%
OATP2B1 inhibitior	+	0.5714	57.14%
OATP1B1 inhibitior	+	0.8358	83.58%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7596	75.96%
P-glycoprotein inhibitior	+	0.6994	69.94%
P-glycoprotein substrate	-	0.5525	55.25%
CYP3A4 substrate	+	0.6472	64.72%
CYP2C9 substrate	-	0.7955	79.55%
CYP2D6 substrate	-	0.8505	85.05%
CYP3A4 inhibition	-	0.8984	89.84%
CYP2C9 inhibition	-	0.5583	55.83%
CYP2C19 inhibition	-	0.5408	54.08%
CYP2D6 inhibition	-	0.8326	83.26%
CYP1A2 inhibition	-	0.6339	63.39%
CYP2C8 inhibition	+	0.7256	72.56%
CYP inhibitory promiscuity	-	0.7598	75.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6645	66.45%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8935	89.35%
Skin irritation	-	0.8029	80.29%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.5164	51.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7051	70.51%
Micronuclear	+	0.7118	71.18%
Hepatotoxicity	-	0.5841	58.41%
skin sensitisation	-	0.8259	82.59%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.9620	96.20%
Acute Oral Toxicity (c)	III	0.3969	39.69%
Estrogen receptor binding	+	0.7799	77.99%
Androgen receptor binding	+	0.7322	73.22%
Thyroid receptor binding	-	0.4918	49.18%
Glucocorticoid receptor binding	-	0.5948	59.48%
Aromatase binding	-	0.5228	52.28%
PPAR gamma	+	0.6852	68.52%
Honey bee toxicity	-	0.7812	78.12%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7050	70.50%
Fish aquatic toxicity	+	0.9906	99.06%

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	99.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.26%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.30%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	95.20%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.86%	94.45%
CHEMBL3194	P02766	Transthyretin	92.37%	90.71%
CHEMBL2581	P07339	Cathepsin D	91.81%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.96%	97.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.97%	97.28%
CHEMBL4208	P20618	Proteasome component C5	87.92%	90.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.56%	95.64%
CHEMBL226	P30542	Adenosine A1 receptor	85.23%	95.93%
CHEMBL340	P08684	Cytochrome P450 3A4	83.80%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.75%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.54%	89.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	83.08%	96.37%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	83.05%	85.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.41%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.03%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.11%	95.17%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 162857563
• LOTUS: LTS0226605
• wikiData: Q105188475