(1R,2S)-1-[3-[(Z)-1-carboxy-2-(3,4-dihydroxyphenyl)ethenoxy]-4-hydroxyphenyl]-6,7-dihydroxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid

Details

• Internal ID: b0c5ef3e-ffb9-4735-b4f8-7244c61663c0
• Taxonomy: Lignans, neolignans and related compounds > Aryltetralin lignans
• IUPAC Name: (1R,2S)-1-[3-[(Z)-1-carboxy-2-(3,4-dihydroxyphenyl)ethenoxy]-4-hydroxyphenyl]-6,7-dihydroxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid
• InChI: InChI=1S/C27H20O12/c28-16-3-1-11(5-18(16)30)6-22(26(35)36)39-21-9-12(2-4-17(21)29)23-14-10-20(32)19(31)8-13(14)7-15(25(33)34)24(23)27(37)38/h1-10,23-24,28-32H,(H,33,34)(H,35,36)(H,37,38)/b22-6-/t23-,24-/m1/s1
• InChI Key: IVVUQFFDRJNNGV-UBHNRUOQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₀O₁₂
• Molecular Weight: 536.40 g/mol
• Exact Mass: 536.09547607 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 3.03
• H-Bond Acceptor: 9
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	-	0.9279	92.79%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8161	81.61%
OATP2B1 inhibitior	+	0.5801	58.01%
OATP1B1 inhibitior	+	0.9228	92.28%
OATP1B3 inhibitior	+	0.9141	91.41%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7416	74.16%
P-glycoprotein inhibitior	+	0.6079	60.79%
P-glycoprotein substrate	-	0.7814	78.14%
CYP3A4 substrate	+	0.5478	54.78%
CYP2C9 substrate	-	0.6084	60.84%
CYP2D6 substrate	-	0.8684	86.84%
CYP3A4 inhibition	-	0.9017	90.17%
CYP2C9 inhibition	+	0.8382	83.82%
CYP2C19 inhibition	-	0.6368	63.68%
CYP2D6 inhibition	-	0.8608	86.08%
CYP1A2 inhibition	+	0.5581	55.81%
CYP2C8 inhibition	+	0.7194	71.94%
CYP inhibitory promiscuity	-	0.5332	53.32%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8697	86.97%
Carcinogenicity (trinary)	Non-required	0.4456	44.56%
Eye corrosion	-	0.9941	99.41%
Eye irritation	-	0.7405	74.05%
Skin irritation	-	0.5897	58.97%
Skin corrosion	-	0.9646	96.46%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7143	71.43%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5024	50.24%
skin sensitisation	-	0.5934	59.34%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6658	66.58%
Acute Oral Toxicity (c)	IV	0.4922	49.22%
Estrogen receptor binding	+	0.7165	71.65%
Androgen receptor binding	+	0.6928	69.28%
Thyroid receptor binding	+	0.5610	56.10%
Glucocorticoid receptor binding	+	0.5596	55.96%
Aromatase binding	-	0.7687	76.87%
PPAR gamma	+	0.6439	64.39%
Honey bee toxicity	-	0.7404	74.04%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.36%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.46%	91.49%
CHEMBL3194	P02766	Transthyretin	94.81%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.28%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.88%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.27%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.63%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.23%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.58%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.16%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.41%	86.33%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.95%	91.03%
CHEMBL340	P08684	Cytochrome P450 3A4	81.43%	91.19%

Plants that contains it

• Bazzania trilobata

Cross-Links

• PubChem: 100918690
• LOTUS: LTS0183007
• wikiData: Q105121327