7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one

Details

• Internal ID: d8d461c1-8847-45de-9775-15033d28954f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)chromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC4=C(C=C3)C(=O)C=C(O4)C5=CC(=C(C=C5)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC4=C(C=C3)C(=O)C=C(O4)C5=CC(=C(C=C5)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)19(9-28)40-27(25)38-12-3-4-13-15(30)8-17(39-18(13)7-12)11-2-5-14(29)16(31)6-11/h2-8,10,19-29,31-36H,9H2,1H3/t10-,19+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
• InChI Key: YYKZZPUWJLNPMU-POFBTZLFSA-N
• Popularity: 0 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: -0.80
• Atomic LogP (AlogP): -1.10
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• 3',4'-Dihydroxy-7-[(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)oxy]flavone
• 7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9251	92.51%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.7015	70.15%
OATP1B1 inhibitior	+	0.9273	92.73%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6446	64.46%
P-glycoprotein inhibitior	-	0.7557	75.57%
P-glycoprotein substrate	-	0.5807	58.07%
CYP3A4 substrate	+	0.6453	64.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8488	84.88%
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	+	0.6587	65.87%
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	-	0.9281	92.81%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4105	41.05%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9258	92.58%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7581	75.81%
Androgen receptor binding	+	0.6484	64.84%
Thyroid receptor binding	+	0.5457	54.57%
Glucocorticoid receptor binding	+	0.5491	54.91%
Aromatase binding	+	0.6023	60.23%
PPAR gamma	+	0.7784	77.84%
Honey bee toxicity	-	0.6600	66.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
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	99.85%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.58%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.33%	89.00%
CHEMBL2581	P07339	Cathepsin D	96.39%	98.95%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	95.89%	83.57%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.76%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.52%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.87%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.92%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.65%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.35%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	89.39%	93.31%
CHEMBL3401	O75469	Pregnane X receptor	87.44%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.32%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.42%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.99%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.01%	95.89%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.91%	80.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.95%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	80.14%	95.93%

Plants that contains it

• Capsella bursa-pastoris
• Lonicera japonica
• Pteris multifida
• Veronicastrum sibiricum

Cross-Links

• PubChem: 16724248
• NPASS: NPC216341