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

Details

• Internal ID: 5171d87a-80d6-493d-9219-2a7f6ffe90a3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)OC5C(C(C(C(O5)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C27H30O15/c28-8-17-20(33)21(34)23(36)27(40-17)42-25-18(9-29)41-26(24(37)22(25)35)38-12-5-13(31)19-14(32)7-15(39-16(19)6-12)10-1-3-11(30)4-2-10/h1-7,17-18,20-31,33-37H,8-9H2/t17-,18-,20-,21+,22-,23-,24-,25-,26-,27+/m1/s1
• InChI Key: YONLJLRPNAUKHY-UZAFNIHYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.13
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6238	62.38%
Caco-2	-	0.9239	92.39%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.6259	62.59%
OATP2B1 inhibitior	-	0.5581	55.81%
OATP1B1 inhibitior	+	0.9447	94.47%
OATP1B3 inhibitior	+	0.9578	95.78%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7678	76.78%
P-glycoprotein inhibitior	-	0.6626	66.26%
P-glycoprotein substrate	-	0.7707	77.07%
CYP3A4 substrate	+	0.6046	60.46%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9399	93.99%
CYP2C9 inhibition	-	0.9431	94.31%
CYP2C19 inhibition	-	0.9201	92.01%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.9283	92.83%
CYP2C8 inhibition	+	0.6886	68.86%
CYP inhibitory promiscuity	-	0.7667	76.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6368	63.68%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.8293	82.93%
Skin corrosion	-	0.9710	97.10%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4082	40.82%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.9071	90.71%
skin sensitisation	-	0.9266	92.66%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8798	87.98%
Acute Oral Toxicity (c)	IV	0.4161	41.61%
Estrogen receptor binding	+	0.7316	73.16%
Androgen receptor binding	+	0.7105	71.05%
Thyroid receptor binding	-	0.5176	51.76%
Glucocorticoid receptor binding	-	0.5612	56.12%
Aromatase binding	+	0.6002	60.02%
PPAR gamma	+	0.7277	72.77%
Honey bee toxicity	-	0.5943	59.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5750	57.50%
Fish aquatic toxicity	+	0.7469	74.69%

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	99.41%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.20%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.39%	89.00%
CHEMBL2581	P07339	Cathepsin D	94.87%	98.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	93.39%	83.57%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.80%	99.15%
CHEMBL3194	P02766	Transthyretin	91.95%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.79%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	90.14%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	89.29%	94.73%
CHEMBL242	Q92731	Estrogen receptor beta	87.71%	98.35%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.30%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.98%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.39%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.85%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.13%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.17%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.41%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.10%	91.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.02%	85.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.84%	97.28%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.76%	90.71%

Plants that contains it

• Aconitum leucostomum
• Aiouea montana
• Aquilegia ecalcarata
• Artemisia szowitziana
• Blumea axillaris
• Ceanothus velutinus
• Chlorophytum borivilianum
• Dipterocarpus dyeri
• Fragaria vesca
• Gamblea innovans
• Garcinia scortechinii
• Gardenia tubifera
• Ipomoea cairica
• Isodon lophanthoides
• Kopsia grandifolia
• Lasianthus fordii
• Ledebouria socialis
• Lycopus europaeus
• Perilla frutescens
• Persea barbujana
• Salvia uliginosa

Cross-Links

• PubChem: 60195926
• NPASS: NPC286212
• LOTUS: LTS0273662
• wikiData: Q105351410