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

Details

• Internal ID: be9c33cd-76f4-4e6e-9577-a43421ac273c
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-7-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=COC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C22H22O11/c1-30-14-4-9(2-3-12(14)24)11-8-31-15-6-10(5-13(25)17(15)18(11)26)32-22-21(29)20(28)19(27)16(7-23)33-22/h2-6,8,16,19-25,27-29H,7H2,1H3/t16-,19-,20+,21+,22-/m1/s1
• InChI Key: APCIHDWWOMFADS-QAGBHRCTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₁
• Molecular Weight: 462.40 g/mol
• Exact Mass: 462.11621151 g/mol
• Topological Polar Surface Area (TPSA): 175.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.06
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.9161	91.61%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	+	0.5872	58.72%
OATP1B1 inhibitior	+	0.9470	94.70%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5983	59.83%
P-glycoprotein inhibitior	-	0.6977	69.77%
P-glycoprotein substrate	-	0.7855	78.55%
CYP3A4 substrate	+	0.6253	62.53%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.7170	71.70%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8755	87.55%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.5982	59.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.4382	43.82%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.7073	70.73%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.5864	58.64%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7788	77.88%
Androgen receptor binding	+	0.5608	56.08%
Thyroid receptor binding	+	0.5974	59.74%
Glucocorticoid receptor binding	+	0.6737	67.37%
Aromatase binding	+	0.5746	57.46%
PPAR gamma	+	0.8124	81.24%
Honey bee toxicity	-	0.7420	74.20%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5449	54.49%
Fish aquatic toxicity	+	0.7079	70.79%

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	98.78%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.48%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.21%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.02%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.26%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.77%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.70%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.74%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.02%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.79%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.15%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.06%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.75%	95.78%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.82%	97.09%
CHEMBL3438	Q05513	Protein kinase C zeta	85.69%	88.48%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.72%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.08%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.77%	97.28%
CHEMBL1907	P15144	Aminopeptidase N	82.16%	93.31%
CHEMBL4208	P20618	Proteasome component C5	82.03%	90.00%
CHEMBL3194	P02766	Transthyretin	81.52%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.44%	90.71%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.37%	95.53%

Plants that contains it

• Thermopsis rhombifolia

Cross-Links

• PubChem: 162948525
• LOTUS: LTS0068258
• wikiData: Q104916183