2-[3-Carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyl]oxybutanedioic acid

Details

• Internal ID: d87d3324-2811-4269-84aa-7ce6c32bf4cd
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: 2-[3-carboxy-4-(3,4-dihydroxyphenyl)-6,7-dihydroxy-3,4-dihydronaphthalene-2-carbonyl]oxybutanedioic acid
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(=CC3=CC(=C(C=C23)O)O)C(=O)OC(CC(=O)O)C(=O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2C(C(=CC3=CC(=C(C=C23)O)O)C(=O)OC(CC(=O)O)C(=O)O)C(=O)O)O)O
• InChI: InChI=1S/C22H18O12/c23-12-2-1-8(4-13(12)24)18-10-6-15(26)14(25)5-9(10)3-11(19(18)21(31)32)22(33)34-16(20(29)30)7-17(27)28/h1-6,16,18-19,23-26H,7H2,(H,27,28)(H,29,30)(H,31,32)
• InChI Key: HYKHDQXNBGOIFP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₁₂
• Molecular Weight: 474.40 g/mol
• Exact Mass: 474.07982601 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.21
• H-Bond Acceptor: 9
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9840	98.40%
Caco-2	-	0.9549	95.49%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7201	72.01%
OATP2B1 inhibitior	+	0.5794	57.94%
OATP1B1 inhibitior	+	0.9073	90.73%
OATP1B3 inhibitior	+	0.9112	91.12%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.7971	79.71%
P-glycoprotein inhibitior	-	0.5794	57.94%
P-glycoprotein substrate	-	0.8096	80.96%
CYP3A4 substrate	+	0.5802	58.02%
CYP2C9 substrate	-	0.5949	59.49%
CYP2D6 substrate	-	0.8604	86.04%
CYP3A4 inhibition	-	0.9277	92.77%
CYP2C9 inhibition	-	0.6097	60.97%
CYP2C19 inhibition	-	0.8670	86.70%
CYP2D6 inhibition	-	0.9185	91.85%
CYP1A2 inhibition	-	0.6913	69.13%
CYP2C8 inhibition	+	0.7083	70.83%
CYP inhibitory promiscuity	-	0.8165	81.65%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9154	91.54%
Carcinogenicity (trinary)	Non-required	0.5513	55.13%
Eye corrosion	-	0.9929	99.29%
Eye irritation	-	0.7447	74.47%
Skin irritation	-	0.7086	70.86%
Skin corrosion	-	0.9532	95.32%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5631	56.31%
Micronuclear	+	0.8218	82.18%
Hepatotoxicity	-	0.6573	65.73%
skin sensitisation	-	0.5867	58.67%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7784	77.84%
Acute Oral Toxicity (c)	III	0.4017	40.17%
Estrogen receptor binding	+	0.7660	76.60%
Androgen receptor binding	+	0.7448	74.48%
Thyroid receptor binding	-	0.5611	56.11%
Glucocorticoid receptor binding	+	0.6461	64.61%
Aromatase binding	-	0.7640	76.40%
PPAR gamma	+	0.5635	56.35%
Honey bee toxicity	-	0.8102	81.02%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6205	62.05%
Fish aquatic toxicity	+	0.9956	99.56%

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	99.35%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	97.06%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.01%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.20%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.31%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.23%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.39%	99.17%
CHEMBL3194	P02766	Transthyretin	85.20%	90.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.57%	94.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%

Plants that contains it

• Lophocolea heterophylla

Cross-Links

• PubChem: 163042439
• LOTUS: LTS0169685
• wikiData: Q104990981