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

Details

• Internal ID: 5ad78a08-6c0e-4e8c-a499-5bf158c8d0cc
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (1R,2S)-3-[(2S,3R,4S,5S)-2-(2-carboxy-2-hydroxyethyl)-4,5-dihydroxyoxan-3-yl]oxycarbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carboxylic acid
• SMILES (Canonical): C1C(C(C(C(O1)CC(C(=O)O)O)OC(=O)C2=CC3=CC(=C(C=C3C(C2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]([C@@H]([C@H]([C@@H](O1)CC(C(=O)O)O)OC(=O)C2=CC3=CC(=C(C=C3[C@H]([C@@H]2C(=O)O)C4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C26H26O14/c27-13-2-1-9(4-14(13)28)20-11-6-16(30)15(29)5-10(11)3-12(21(20)25(36)37)26(38)40-23-19(7-17(31)24(34)35)39-8-18(32)22(23)33/h1-6,17-23,27-33H,7-8H2,(H,34,35)(H,36,37)/t17?,18-,19-,20+,21+,22-,23-/m0/s1
• InChI Key: ZRVQPXBHLQIZMJ-ABVFIXOBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₆O₁₄
• Molecular Weight: 562.50 g/mol
• Exact Mass: 562.13225550 g/mol
• Topological Polar Surface Area (TPSA): 252.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.39
• H-Bond Acceptor: 12
• H-Bond Donor: 9
• Rotatable Bonds: 7

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	-	0.9367	93.67%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7486	74.86%
OATP2B1 inhibitior	-	0.6945	69.45%
OATP1B1 inhibitior	+	0.8715	87.15%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8110	81.10%
P-glycoprotein inhibitior	-	0.5066	50.66%
P-glycoprotein substrate	-	0.6031	60.31%
CYP3A4 substrate	+	0.6458	64.58%
CYP2C9 substrate	-	0.7958	79.58%
CYP2D6 substrate	-	0.8503	85.03%
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	+	0.6483	64.83%
CYP inhibitory promiscuity	-	0.7598	75.98%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6645	66.45%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.8832	88.32%
Skin irritation	-	0.8029	80.29%
Skin corrosion	-	0.9539	95.39%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6964	69.64%
Micronuclear	+	0.7118	71.18%
Hepatotoxicity	-	0.7161	71.61%
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	-	0.9367	93.67%
Acute Oral Toxicity (c)	III	0.3969	39.69%
Estrogen receptor binding	+	0.7782	77.82%
Androgen receptor binding	+	0.6594	65.94%
Thyroid receptor binding	-	0.5137	51.37%
Glucocorticoid receptor binding	-	0.5948	59.48%
Aromatase binding	-	0.6898	68.98%
PPAR gamma	+	0.6234	62.34%
Honey bee toxicity	-	0.7529	75.29%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6850	68.50%
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	99.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.11%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.20%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	94.57%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.48%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.98%	94.45%
CHEMBL2581	P07339	Cathepsin D	92.23%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.91%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	89.73%	95.93%
CHEMBL1951	P21397	Monoamine oxidase A	86.89%	91.49%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.37%	89.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.94%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	84.83%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.76%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.76%	97.28%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.56%	96.38%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.47%	85.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.39%	95.89%
CHEMBL4208	P20618	Proteasome component C5	81.71%	90.00%
CHEMBL3194	P02766	Transthyretin	81.31%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.28%	90.71%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.83%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.81%	86.33%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.68%	97.53%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.55%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.33%	95.56%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	80.24%	83.00%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 100918688
• LOTUS: LTS0229823
• wikiData: Q105382276