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

Details

• Internal ID: 39997887-d055-45b0-8937-657d3b797fab
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-(4-hydroxyphenyl)-5-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC2=C1C(=O)C(=CO2)C3=CC=C(C=C3)O)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC2=C1C(=O)C(=CO2)C3=CC=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C22H22O10/c1-29-14-6-12(31-22-21(28)20(27)19(26)16(8-23)32-22)7-15-17(14)18(25)13(9-30-15)10-2-4-11(24)5-3-10/h2-7,9,16,19-24,26-28H,8H2,1H3/t16-,19-,20+,21-,22-/m1/s1
• InChI Key: KSVVGBSBNPMXJF-RECXWPGBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• 128856-77-9
• 3-(4-hydroxyphenyl)-5-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 7-O-beta-glucopyranosyl-4/'-hydroxy-5-methoxyisoflavone
• 7-O-beta-Glucopyranosyl-4'-hydroxy-5-methoxyisoflavone
• 5-O-Methylgenistin
• MEGxp0_000225
• CHEMBL4161741
• ACon1_000200
• DTXSID90926220
• NCGC00180788-01
• Isoprunetin 7-O-glucoside, >=90% (LC/MS-ELSD)
• BRD-K31181727-001-01-6
• 3-(4-Hydroxyphenyl)-5-methoxy-4-oxo-4H-1-benzopyran-7-yl hexopyranoside
• 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-5-methoxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8889	88.89%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5570	55.70%
OATP1B1 inhibitior	+	0.9488	94.88%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.8137	81.37%
P-glycoprotein inhibitior	-	0.6456	64.56%
P-glycoprotein substrate	-	0.8092	80.92%
CYP3A4 substrate	+	0.6244	62.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8324	83.24%
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	+	0.6874	68.74%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9257	92.57%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3897	38.97%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.7073	70.73%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.4887	48.87%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7701	77.01%
Androgen receptor binding	+	0.7188	71.88%
Thyroid receptor binding	+	0.5625	56.25%
Glucocorticoid receptor binding	+	0.7592	75.92%
Aromatase binding	+	0.6043	60.43%
PPAR gamma	+	0.7710	77.10%
Honey bee toxicity	-	0.7365	73.65%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5049	50.49%
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	98.58%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.36%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.27%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.48%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.47%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.63%	86.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.05%	96.21%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.63%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.12%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.78%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.62%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.90%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.35%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.10%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.66%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.54%	99.15%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.10%	97.28%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.66%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.32%	91.71%

Plants that contains it

• Eriosema tuberosum
• Heliotropium hirsutissimum
• Inulanthera calva
• Nicotiana raimondii
• Ormosia henryi
• Scolopia chinensis
• Trollius europaeus
• Ulex europaeus

Cross-Links

• PubChem: 189922
• NPASS: NPC100720
• LOTUS: LTS0172993
• wikiData: Q82900712