3-(4-Methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

Details

• Internal ID: 0c864874-bab9-4f1b-ace2-466d8ddd2e0b
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O
• InChI: InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3
• InChI Key: MGJLSBDCWOSMHL-UHFFFAOYSA-N
• Popularity: 82 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₉
• Molecular Weight: 430.40 g/mol
• Exact Mass: 430.12638228 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 0.65
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 486-62-4
• Formononetin 7-O-beta-D-glucopyranoside
• 3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl hexopyranoside
• 3-(4-methoxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 1084808-15-0
• 3-(4-Methoxyphenyl)-7-((3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• Formononetin-7-glucoside
• C22H22O9
• Ononin?
• Oprea1_111850
• Oprea1_697373
• MLS001194859
• SCHEMBL13169519
• HMS2874C17
• HMS3341O02
• BCP10844
• STK976270
• AKOS001578228
• SMR000554684
• O0405
• AB00822826-06
• Formononetin glucoside;Formononetin-7-glucoside;Ononoside;Biochanin B;Neochanin;Formononetin-7-O-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8314	83.14%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.6943	69.43%
OATP1B1 inhibitior	+	0.9426	94.26%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5863	58.63%
P-glycoprotein inhibitior	-	0.6823	68.23%
P-glycoprotein substrate	-	0.8985	89.85%
CYP3A4 substrate	+	0.6184	61.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8291	82.91%
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	-	0.6012	60.12%
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	-	0.9312	93.12%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4790	47.90%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6073	60.73%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7067	70.67%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7975	79.75%
Androgen receptor binding	+	0.7483	74.83%
Thyroid receptor binding	+	0.5353	53.53%
Glucocorticoid receptor binding	+	0.7164	71.64%
Aromatase binding	+	0.5815	58.15%
PPAR gamma	+	0.7519	75.19%
Honey bee toxicity	-	0.8448	84.48%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7079	70.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5880	P60568	Interleukin-2	120 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.67%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.36%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.90%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.54%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.15%	89.00%
CHEMBL1907	P15144	Aminopeptidase N	91.67%	93.31%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.15%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.89%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.48%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.51%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.05%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.26%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.67%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.13%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.91%	96.21%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.69%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	82.01%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.47%	90.00%

Plants that contains it

• Ammopiptanthus mongolicus
• Amorpha fruticosa
• Baptisia australis
• Butea monosperma
• Caragana conferta
• Cicer judaicum
• Cicer songaricum
• Deguelia scandens
• Glycine max
• Glycyrrhiza glabra
• Glycyrrhiza pallidiflora
• Glycyrrhiza uralensis
• Hedysarum polybotrys
• Maackia amurensis
• Mucuna birdwoodiana
• Podocytisus caramanicus
• Styphnolobium japonicum
• Thermopsis alterniflora
• Trifolium aureum
• Trifolium montanum
• Trifolium pratense
• Trifolium resupinatum
• Trifolium subterraneum
• Vigna radiata var. radiata
• Wisteria brachybotrys
• Xanthium strumarium

Cross-Links

• PubChem: 3733033
• NPASS: NPC198030
• LOTUS: LTS0065177
• wikiData: Q104393076