(2R)-2-[(1R,2S)-3-[(1R)-1-carboxylato-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoate

Details

• Internal ID: 8369e5c0-3318-4a7f-9039-b75718da407f
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (2R)-2-[(1R,2S)-3-[(1R)-1-carboxylato-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl-1-(3,4-dihydroxyphenyl)-6,7-dihydroxy-1,2-dihydronaphthalene-2-carbonyl]oxy-3-(3,4-dihydroxyphenyl)propanoate
• 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)O)C5=CC(=C(C=C5)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)[O-])OC(=O)[C@H]2[C@@H](C3=CC(=C(C=C3C=C2C(=O)O[C@H](CC4=CC(=C(C=C4)O)O)C(=O)[O-])O)O)C5=CC(=C(C=C5)O)O)O)O
• InChI: InChI=1S/C36H30O16/c37-21-4-1-15(7-24(21)40)9-29(33(45)46)51-35(49)20-11-18-13-27(43)28(44)14-19(18)31(17-3-6-23(39)26(42)12-17)32(20)36(50)52-30(34(47)48)10-16-2-5-22(38)25(41)8-16/h1-8,11-14,29-32,37-44H,9-10H2,(H,45,46)(H,47,48)/p-2/t29-,30-,31-,32-/m1/s1
• InChI Key: VKWZFIDWHLCPHJ-SEVDZJIVSA-L
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₂₈O₁₆-₂
• Molecular Weight: 716.60 g/mol
• Exact Mass: 716.13773480 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 0.29
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8839	88.39%
Caco-2	-	0.9074	90.74%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7547	75.47%
OATP2B1 inhibitior	-	0.5647	56.47%
OATP1B1 inhibitior	+	0.8986	89.86%
OATP1B3 inhibitior	+	0.9341	93.41%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8419	84.19%
P-glycoprotein inhibitior	+	0.7408	74.08%
P-glycoprotein substrate	-	0.6658	66.58%
CYP3A4 substrate	+	0.6131	61.31%
CYP2C9 substrate	-	0.5987	59.87%
CYP2D6 substrate	-	0.8679	86.79%
CYP3A4 inhibition	-	0.8625	86.25%
CYP2C9 inhibition	+	0.7206	72.06%
CYP2C19 inhibition	-	0.7601	76.01%
CYP2D6 inhibition	-	0.8233	82.33%
CYP1A2 inhibition	-	0.5598	55.98%
CYP2C8 inhibition	+	0.7398	73.98%
CYP inhibitory promiscuity	-	0.5545	55.45%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8797	87.97%
Carcinogenicity (trinary)	Non-required	0.5166	51.66%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8776	87.76%
Skin irritation	-	0.7021	70.21%
Skin corrosion	-	0.9541	95.41%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8193	81.93%
Micronuclear	+	0.7718	77.18%
Hepatotoxicity	-	0.5698	56.98%
skin sensitisation	-	0.6976	69.76%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7054	70.54%
Acute Oral Toxicity (c)	III	0.4761	47.61%
Estrogen receptor binding	+	0.8034	80.34%
Androgen receptor binding	+	0.7868	78.68%
Thyroid receptor binding	+	0.5157	51.57%
Glucocorticoid receptor binding	+	0.5628	56.28%
Aromatase binding	-	0.6322	63.22%
PPAR gamma	+	0.6864	68.64%
Honey bee toxicity	-	0.6104	61.04%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5550	55.50%
Fish aquatic toxicity	+	0.9973	99.73%

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	98.50%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.87%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.68%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.01%	95.17%
CHEMBL2581	P07339	Cathepsin D	92.69%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.47%	99.15%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.66%	89.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.96%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.86%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	87.51%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.77%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.32%	96.95%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.32%	97.28%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.20%	86.92%
CHEMBL340	P08684	Cytochrome P450 3A4	82.10%	91.19%
CHEMBL3194	P02766	Transthyretin	81.94%	90.71%
CHEMBL2535	P11166	Glucose transporter	81.15%	98.75%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.20%	90.24%

Plants that contains it

• Arnebia euchroma
• Eucalyptus coccifera
• Lithospermum erythrorhizon
• Rhizomnium magnifolium

Cross-Links

• PubChem: 5320234
• NPASS: NPC266082