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

Details

• Internal ID: 4dc585f1-feb5-42c9-bc79-59a2cb31ef12
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxy-3-methylphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O
• SMILES (Isomeric): CC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
• InChI: InChI=1S/C22H22O10/c1-9-4-10(2-3-12(9)24)15-7-14(26)18-13(25)5-11(6-16(18)31-15)30-22-21(29)20(28)19(27)17(8-23)32-22/h2-7,17,19-25,27-29H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
• InChI Key: VZALAWNLGKUHQV-MIUGBVLSSA-N
• Popularity: 0 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): 166.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.36
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.8871	88.71%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	+	0.5937	59.37%
OATP1B1 inhibitior	+	0.9505	95.05%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5756	57.56%
P-glycoprotein inhibitior	-	0.8037	80.37%
P-glycoprotein substrate	-	0.7614	76.14%
CYP3A4 substrate	+	0.5792	57.92%
CYP2C9 substrate	-	0.6986	69.86%
CYP2D6 substrate	-	0.8617	86.17%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.6820	68.20%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9249	92.49%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5382	53.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.5095	50.95%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8821	88.21%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7763	77.63%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7579	75.79%
Androgen receptor binding	+	0.6823	68.23%
Thyroid receptor binding	+	0.5501	55.01%
Glucocorticoid receptor binding	+	0.6740	67.40%
Aromatase binding	+	0.6082	60.82%
PPAR gamma	+	0.7941	79.41%
Honey bee toxicity	-	0.7644	76.44%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.03%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.85%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	96.77%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.31%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.62%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.72%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	94.62%	94.73%
CHEMBL220	P22303	Acetylcholinesterase	91.91%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.90%	96.21%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	89.85%	83.57%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.81%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.37%	86.92%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	86.70%	93.65%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.47%	97.09%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.45%	95.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.93%	85.14%
CHEMBL3194	P02766	Transthyretin	85.79%	90.71%
CHEMBL3714130	P46095	G-protein coupled receptor 6	84.36%	97.36%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.75%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.22%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.17%	99.17%

Plants that contains it

• Spiraea brahuica

Cross-Links

• PubChem: 101563016
• LOTUS: LTS0155736
• wikiData: Q105299586