5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypyrano[2,3-h]chromen-4-one

Details

• Internal ID: a9ac739c-254d-4e74-aa4f-77fc7e3b1e01
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxypyrano[2,3-h]chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC4=C3C=CC(O4)(C)C)O)C5=CC=C(C=C5)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)OC2=C(OC3=C(C2=O)C(=CC4=C3C=CC(O4)(C)C)O)C5=CC=C(C=C5)O)O)O)O
• InChI: InChI=1S/C26H26O10/c1-11-18(29)20(31)21(32)25(33-11)35-24-19(30)17-15(28)10-16-14(8-9-26(2,3)36-16)23(17)34-22(24)12-4-6-13(27)7-5-12/h4-11,18,20-21,25,27-29,31-32H,1-3H3/t11-,18-,20+,21+,25+/m0/s1
• InChI Key: FRKNVAWDQIICIE-ZNLMPTLISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₆O₁₀
• Molecular Weight: 498.50 g/mol
• Exact Mass: 498.15259702 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.26
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9085	90.85%
Caco-2	-	0.8454	84.54%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7088	70.88%
OATP2B1 inhibitior	-	0.5584	55.84%
OATP1B1 inhibitior	+	0.9045	90.45%
OATP1B3 inhibitior	+	0.8917	89.17%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.6880	68.80%
P-glycoprotein inhibitior	+	0.6373	63.73%
P-glycoprotein substrate	+	0.5160	51.60%
CYP3A4 substrate	+	0.6614	66.14%
CYP2C9 substrate	-	0.8465	84.65%
CYP2D6 substrate	-	0.8507	85.07%
CYP3A4 inhibition	-	0.6286	62.86%
CYP2C9 inhibition	-	0.7684	76.84%
CYP2C19 inhibition	-	0.6695	66.95%
CYP2D6 inhibition	-	0.9251	92.51%
CYP1A2 inhibition	-	0.8583	85.83%
CYP2C8 inhibition	+	0.7854	78.54%
CYP inhibitory promiscuity	-	0.5409	54.09%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Danger	0.4384	43.84%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.8222	82.22%
Skin irritation	-	0.7568	75.68%
Skin corrosion	-	0.9377	93.77%
Ames mutagenesis	+	0.5126	51.26%
Human Ether-a-go-go-Related Gene inhibition	-	0.5841	58.41%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	-	0.6449	64.49%
skin sensitisation	-	0.8402	84.02%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6615	66.15%
Acute Oral Toxicity (c)	III	0.6283	62.83%
Estrogen receptor binding	+	0.7326	73.26%
Androgen receptor binding	+	0.7372	73.72%
Thyroid receptor binding	+	0.6440	64.40%
Glucocorticoid receptor binding	+	0.8046	80.46%
Aromatase binding	+	0.6069	60.69%
PPAR gamma	+	0.6889	68.89%
Honey bee toxicity	-	0.7295	72.95%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5350	53.50%
Fish aquatic toxicity	+	0.9887	98.87%

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	99.71%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.77%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.41%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.65%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	93.51%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.88%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.79%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.93%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.82%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.45%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.31%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.83%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.17%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.62%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.40%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.84%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.38%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.04%	95.89%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	82.04%	92.78%
CHEMBL242	Q92731	Estrogen receptor beta	81.59%	98.35%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.16%	93.10%

Plants that contains it

• Epimedium grandiflorum

Cross-Links

• PubChem: 162998938
• LOTUS: LTS0104655
• wikiData: Q105000221