3-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: a8e679b5-774d-46f9-a85b-b52b6f2cec78
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-6-15-18(27)19(28)20(29)21(32-15)31-9-4-13(25)16-14(5-9)30-7-10(17(16)26)8-1-2-11(23)12(24)3-8/h1-5,7,15,18-25,27-29H,6H2/t15-,18-,19+,20-,21-/m1/s1
• InChI Key: WJHSRFQBVYHKKL-CMWLGVBASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• 3-(3,4-Dihydroxyphenyl)-5-hydroxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 3-(3,4-dihydroxyphenyl)-5-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9407	94.07%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5921	59.21%
OATP1B1 inhibitior	+	0.9566	95.66%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5557	55.57%
P-glycoprotein inhibitior	-	0.7939	79.39%
P-glycoprotein substrate	-	0.8920	89.20%
CYP3A4 substrate	+	0.6065	60.65%
CYP2C9 substrate	-	0.6709	67.09%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.6933	69.33%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8353	83.53%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5143	51.43%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7571	75.71%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.5966	59.66%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7335	73.35%
Androgen receptor binding	+	0.6661	66.61%
Thyroid receptor binding	+	0.6043	60.43%
Glucocorticoid receptor binding	+	0.6582	65.82%
Aromatase binding	+	0.6036	60.36%
PPAR gamma	+	0.7875	78.75%
Honey bee toxicity	-	0.6839	68.39%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.40%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.25%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.73%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.49%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	90.65%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.10%	97.09%
CHEMBL1951	P21397	Monoamine oxidase A	89.93%	91.49%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	89.15%	95.78%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.89%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.44%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.95%	99.17%
CHEMBL3194	P02766	Transthyretin	85.33%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.69%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.20%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.15%	97.28%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.38%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	81.49%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	80.73%	95.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.12%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.08%	95.89%

Plants that contains it

• Maclura tinctoria
• Marchantia polymorpha

Cross-Links

• PubChem: 12313772
• LOTUS: LTS0169689
• wikiData: Q105306786