5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

Details

• Internal ID: cefcc0a7-44f8-4983-a675-2af18105ae64
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=C(C=C3)O)C4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=C(C2=C(C(=C1)O)C(=O)C=C(O2)C3=CC=C(C=C3)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C22H22O10/c1-30-14-7-12(26)16-11(25)6-13(9-2-4-10(24)5-3-9)31-21(16)17(14)22-20(29)19(28)18(27)15(8-23)32-22/h2-7,15,18-20,22-24,26-29H,8H2,1H3/t15-,18-,19+,20-,22+/m1/s1
• InChI Key: HHPLIFSIFJSIBY-PGPONNFDSA-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: 0.50
• Atomic LogP (AlogP): 0.39
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 4

Synonyms

• 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6545	65.45%
Caco-2	-	0.8123	81.23%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6233	62.33%
OATP2B1 inhibitior	-	0.5477	54.77%
OATP1B1 inhibitior	+	0.8169	81.69%
OATP1B3 inhibitior	+	0.9830	98.30%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7304	73.04%
P-glycoprotein inhibitior	-	0.5378	53.78%
P-glycoprotein substrate	-	0.7092	70.92%
CYP3A4 substrate	+	0.6078	60.78%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8299	82.99%
CYP3A4 inhibition	-	0.7983	79.83%
CYP2C9 inhibition	-	0.8483	84.83%
CYP2C19 inhibition	-	0.8386	83.86%
CYP2D6 inhibition	-	0.9339	93.39%
CYP1A2 inhibition	-	0.8015	80.15%
CYP2C8 inhibition	+	0.7225	72.25%
CYP inhibitory promiscuity	-	0.6314	63.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6988	69.88%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.8711	87.11%
Skin irritation	-	0.8040	80.40%
Skin corrosion	-	0.9556	95.56%
Ames mutagenesis	+	0.5899	58.99%
Human Ether-a-go-go-Related Gene inhibition	-	0.4675	46.75%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9200	92.00%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6347	63.47%
Acute Oral Toxicity (c)	III	0.6599	65.99%
Estrogen receptor binding	+	0.6996	69.96%
Androgen receptor binding	+	0.7970	79.70%
Thyroid receptor binding	-	0.5090	50.90%
Glucocorticoid receptor binding	+	0.6844	68.44%
Aromatase binding	-	0.4910	49.10%
PPAR gamma	+	0.6468	64.68%
Honey bee toxicity	-	0.7189	71.89%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6249	62.49%
Fish aquatic toxicity	-	0.4258	42.58%

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	98.73%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.29%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.02%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.42%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.63%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.38%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.85%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.43%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.82%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.44%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.92%	96.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.68%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	85.49%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.99%	97.14%
CHEMBL3194	P02766	Transthyretin	83.99%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.90%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.86%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.52%	95.89%

Plants that contains it

• Gmelina arborea
• Gnetum africanum
• Iris florentina
• Trollius ledebourii
• Zantedeschia aethiopica

Cross-Links

• PubChem: 14583621
• NPASS: NPC282012
• LOTUS: LTS0001882
• wikiData: Q105028452