Yuanhuanin

Details

• Internal ID: e13e0b5c-63ca-4987-ac50-ab3655cba3c6
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 2-(3,4-dihydroxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC2=C(C(=C1)OC3C(C(C(C(O3)CO)O)O)O)C(=O)C=C(O2)C4=CC(=C(C=C4)O)O
• SMILES (Isomeric): COC1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)C=C(O2)C4=CC(=C(C=C4)O)O
• InChI: InChI=1S/C22H22O11/c1-30-10-5-15-18(13(26)7-14(31-15)9-2-3-11(24)12(25)4-9)16(6-10)32-22-21(29)20(28)19(27)17(8-23)33-22/h2-7,17,19-25,27-29H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
• InChI Key: ZXVSQQSRCKKYLS-MIUGBVLSSA-N
• Popularity: 2 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: 0.30
• Atomic LogP (AlogP): 0.06
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• 83133-14-6
• 3'-Hydroxygenkwanin 5-O-beta-glucoside
• DTXSID501003149
• AKOS040763567
• 2-(3,4-dihydroxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• HY-121386
• Luteolin 7-methyl ether 5-O-beta-glucoside
• CS-0081842
• 2-(3,4-Dihydroxyphenyl)-7-methoxy-4-oxo-4H-1-benzopyran-5-yl hexopyranoside
• 4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-(.beta.-D-glucopyranosyloxy)-7-methoxy-
• 2-(3,4-dihydroxyphenyl)-7-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8961	89.61%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5506	55.06%
OATP1B1 inhibitior	+	0.9135	91.35%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5805	58.05%
P-glycoprotein inhibitior	-	0.5726	57.26%
P-glycoprotein substrate	-	0.7434	74.34%
CYP3A4 substrate	+	0.5752	57.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
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	+	0.6265	62.65%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8983	89.83%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4712	47.12%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7941	79.41%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7490	74.90%
Androgen receptor binding	+	0.7448	74.48%
Thyroid receptor binding	+	0.5508	55.08%
Glucocorticoid receptor binding	+	0.7360	73.60%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7386	73.86%
Honey bee toxicity	-	0.7437	74.37%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6949	69.49%
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	99.52%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.47%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.98%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.82%	94.00%
CHEMBL2581	P07339	Cathepsin D	94.80%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.34%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.47%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.17%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.94%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	88.24%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.01%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.64%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.92%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.72%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.66%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL3194	P02766	Transthyretin	83.48%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.13%	94.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.56%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	80.37%	93.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.23%	90.71%

Plants that contains it

• Daphne feddei
• Daphne sericea
• Solanum aculeatissimum
• Wikstroemia canescens

Cross-Links

• PubChem: 179680
• NPASS: NPC54889
• LOTUS: LTS0086602
• wikiData: Q82997581