5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-7-[(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one

Details

• Internal ID: a992a86d-c9f9-48e6-8dbb-104a802dfc3a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-3-[(2S,3S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-7-[(2S,4S,5R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• SMILES (Isomeric): CC1[C@@H]([C@@H](C([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@H](C([C@H](C(O4)C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• InChI: InChI=1S/C27H30O14/c1-9-17(30)20(33)22(35)26(37-9)39-13-7-14(29)16-15(8-13)40-24(11-3-5-12(28)6-4-11)25(19(16)32)41-27-23(36)21(34)18(31)10(2)38-27/h3-10,17-18,20-23,26-31,33-36H,1-2H3/t9?,10?,17-,18-,20-,21?,22?,23-,26-,27-/m0/s1
• InChI Key: PUPKKEQDLNREIM-YMCFDUETSA-N
• Popularity: 59 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 5

Synonyms

• SCHEMBL244260
• LMPK12111865

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8072	80.72%
Caco-2	-	0.8952	89.52%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7235	72.35%
OATP2B1 inhibitior	-	0.5524	55.24%
OATP1B1 inhibitior	+	0.9325	93.25%
OATP1B3 inhibitior	+	0.8556	85.56%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8860	88.60%
P-glycoprotein inhibitior	-	0.4690	46.90%
P-glycoprotein substrate	-	0.6551	65.51%
CYP3A4 substrate	+	0.6073	60.73%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.6813	68.13%
CYP2C9 inhibition	-	0.8866	88.66%
CYP2C19 inhibition	-	0.8648	86.48%
CYP2D6 inhibition	-	0.9418	94.18%
CYP1A2 inhibition	-	0.6999	69.99%
CYP2C8 inhibition	+	0.7996	79.96%
CYP inhibitory promiscuity	-	0.5626	56.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6369	63.69%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.8790	87.90%
Skin irritation	-	0.6827	68.27%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	+	0.5363	53.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.3770	37.70%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8967	89.67%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7779	77.79%
Acute Oral Toxicity (c)	III	0.4830	48.30%
Estrogen receptor binding	+	0.6962	69.62%
Androgen receptor binding	+	0.6657	66.57%
Thyroid receptor binding	+	0.5238	52.38%
Glucocorticoid receptor binding	+	0.6285	62.85%
Aromatase binding	-	0.5056	50.56%
PPAR gamma	+	0.7048	70.48%
Honey bee toxicity	-	0.8043	80.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5250	52.50%
Fish aquatic toxicity	+	0.9566	95.66%

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	98.79%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.74%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.26%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.76%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.54%	94.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.73%	95.64%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.06%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.07%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.20%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.42%	95.78%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.03%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.31%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.96%	90.71%
CHEMBL242	Q92731	Estrogen receptor beta	84.52%	98.35%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.07%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.51%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.21%	99.17%
CHEMBL3194	P02766	Transthyretin	83.21%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.39%	90.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.23%	93.65%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.22%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.92%	99.23%

Plants that contains it

• Adesmia incana
• Aesculus hippocastanum
• Alpinia officinarum
• Asplenium viride
• Bauhinia forficata
• Bupleurum chinense
• Camellia sinensis
• Chelidonium majus
• Chengiopanax sciadophylloides
• Chenopodium murale
• Chromolaena subscandens
• Cleome amblyocarpa
• Dorycnium pentaphyllum subsp. herbaceum
• Epimedium acuminatum
• Epimedium brevicornu
• Eryngium campestre
• Eryngium planum
• Ficus septica
• Garcinia dulcis
• Geranium nepalense
• Geranium thunbergii
• Hibiscus cannabinus
• Houttuynia cordata
• Justicia spicigera
• Kaempferia galanga
• Lespedeza cyrtobotrya
• Lespedeza virgata
• Ligustrum vulgare
• Lysimachia christinae
• Ostericum sieboldii
• Panax trifolius
• Pilularia globulifera
• Prunus japonica
• Prunus spinosa
• Tephrosia nubica
• Tilia tomentosa
• Vancouveria hexandra
• Viola diamantiaca

Cross-Links

• PubChem: 44258935
• NPASS: NPC251065
• LOTUS: LTS0269109
• wikiData: Q104388244