3,4-Dihydroxy-1-[4-hydroxy-5-(3-hydroxy-2,5-dimethoxyphenoxy)-2-methoxyphenyl]-2-methoxyxanthen-9-one

Details

• Internal ID: 52b8fa2d-a65a-415e-94bb-4ed7f9746bad
• Taxonomy: Phenylpropanoids and polyketides > Tannins
• IUPAC Name: 3,4-dihydroxy-1-[4-hydroxy-5-(3-hydroxy-2,5-dimethoxyphenoxy)-2-methoxyphenyl]-2-methoxyxanthen-9-one
• SMILES (Canonical): COC1=CC(=C(C(=C1)OC2=C(C=C(C(=C2)C3=C4C(=C(C(=C3OC)O)O)OC5=CC=CC=C5C4=O)OC)O)OC)O
• SMILES (Isomeric): COC1=CC(=C(C(=C1)OC2=C(C=C(C(=C2)C3=C4C(=C(C(=C3OC)O)O)OC5=CC=CC=C5C4=O)OC)O)OC)O
• InChI: InChI=1S/C29H24O11/c1-35-13-9-17(31)27(37-3)21(10-13)39-20-11-15(19(36-2)12-16(20)30)22-23-24(32)14-7-5-6-8-18(14)40-29(23)26(34)25(33)28(22)38-4/h5-12,30-31,33-34H,1-4H3
• InChI Key: WYSSKHUCUAFSDU-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₄O₁₁
• Molecular Weight: 548.50 g/mol
• Exact Mass: 548.13186158 g/mol
• Topological Polar Surface Area (TPSA): 153.00 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 5.26
• H-Bond Acceptor: 11
• H-Bond Donor: 4
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9464	94.64%
Caco-2	-	0.7031	70.31%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7784	77.84%
OATP2B1 inhibitior	-	0.5702	57.02%
OATP1B1 inhibitior	+	0.8488	84.88%
OATP1B3 inhibitior	+	0.9791	97.91%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9367	93.67%
P-glycoprotein inhibitior	+	0.8977	89.77%
P-glycoprotein substrate	-	0.6415	64.15%
CYP3A4 substrate	+	0.6613	66.13%
CYP2C9 substrate	-	0.8329	83.29%
CYP2D6 substrate	-	0.7966	79.66%
CYP3A4 inhibition	-	0.7900	79.00%
CYP2C9 inhibition	-	0.8973	89.73%
CYP2C19 inhibition	-	0.7079	70.79%
CYP2D6 inhibition	-	0.9069	90.69%
CYP1A2 inhibition	+	0.8325	83.25%
CYP2C8 inhibition	+	0.7952	79.52%
CYP inhibitory promiscuity	+	0.5295	52.95%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6022	60.22%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.8152	81.52%
Skin irritation	-	0.7279	72.79%
Skin corrosion	-	0.9633	96.33%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6734	67.34%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.5034	50.34%
skin sensitisation	-	0.9405	94.05%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.4679	46.79%
Acute Oral Toxicity (c)	II	0.4732	47.32%
Estrogen receptor binding	+	0.9114	91.14%
Androgen receptor binding	+	0.7603	76.03%
Thyroid receptor binding	+	0.6215	62.15%
Glucocorticoid receptor binding	+	0.8722	87.22%
Aromatase binding	+	0.6696	66.96%
PPAR gamma	+	0.7071	70.71%
Honey bee toxicity	-	0.8177	81.77%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6051	60.51%
Fish aquatic toxicity	+	0.9122	91.22%

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	99.55%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.93%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.30%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.11%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.26%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.84%	99.23%
CHEMBL2581	P07339	Cathepsin D	93.84%	98.95%
CHEMBL2535	P11166	Glucose transporter	92.20%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.03%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.42%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.49%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.44%	92.62%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.42%	93.65%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.74%	92.67%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.03%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	83.69%	94.73%
CHEMBL4208	P20618	Proteasome component C5	83.33%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.02%	95.50%
CHEMBL2056	P21728	Dopamine D1 receptor	82.29%	91.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.07%	96.67%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	81.83%	94.23%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	81.27%	98.21%
CHEMBL3194	P02766	Transthyretin	80.57%	90.71%
CHEMBL3192	Q9BY41	Histone deacetylase 8	80.33%	93.99%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	80.01%	98.11%

Plants that contains it

• Hypericum monogynum

Cross-Links

• PubChem: 44513408
• LOTUS: LTS0083703
• wikiData: Q105322528