Quercetin 3-neohesperidoside

Details

• Internal ID: eceb306d-8778-4dda-a61e-67dba367872c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(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)-5,7-dihydroxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)O)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=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H30O16/c1-8-17(33)20(36)22(38)26(39-8)43-25-21(37)18(34)15(7-28)41-27(25)42-24-19(35)16-13(32)5-10(29)6-14(16)40-23(24)9-2-3-11(30)12(31)4-9/h2-6,8,15,17-18,20-22,25-34,36-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,25+,26-,27-/m0/s1
• InChI Key: FYBMGZSDYDNBFX-GXPPAHCZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₆
• Molecular Weight: 610.50 g/mol
• Exact Mass: 610.15338487 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.69
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 6

Synonyms

• 32453-36-4
• Quercetin 3-neohesperidoside
• Quercetin-3-O-neohesperidin
• Quercetin 3-rhamnosylglucoside
• Quercetin 3-O-rhamnosylglucoside
• 29662-79-1
• 3-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-oxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chromen-4-one
• C27H30O16
• 3-(((2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 3-((O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
• 3-[(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)-5,7-dihydroxychromen-4-one
• 3-O-Neohesperidoside Quercetin
• DTXSID70952123
• HY-N7976
• AKOS040760121
• MS-30696
• CS-0138909
• E80608
• Q63393010
• 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl 2-O-(6-deoxyhexopyranosyl)hexopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9170	91.70%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.5611	56.11%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7531	75.31%
P-glycoprotein inhibitior	-	0.5944	59.44%
P-glycoprotein substrate	-	0.5450	54.50%
CYP3A4 substrate	+	0.6636	66.36%
CYP2C9 substrate	-	0.6847	68.47%
CYP2D6 substrate	-	0.8618	86.18%
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	+	0.8435	84.35%
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	-	0.9056	90.56%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	+	0.5163	51.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.6458	64.58%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9124	91.24%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.8269	82.69%
Androgen receptor binding	+	0.6600	66.00%
Thyroid receptor binding	+	0.5456	54.56%
Glucocorticoid receptor binding	+	0.5975	59.75%
Aromatase binding	+	0.6179	61.79%
PPAR gamma	+	0.7400	74.00%
Honey bee toxicity	-	0.7074	70.74%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5550	55.50%
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	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.20%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.91%	89.00%
CHEMBL2581	P07339	Cathepsin D	97.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.05%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.01%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.99%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.05%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.88%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.57%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.51%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	85.53%	97.36%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	85.21%	95.64%
CHEMBL3194	P02766	Transthyretin	84.38%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.92%	86.92%
CHEMBL4208	P20618	Proteasome component C5	81.18%	90.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.90%	95.78%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.77%	80.78%

Plants that contains it

• Acer mandshuricum
• Alkanna cappadocica
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Calendula officinalis
• Clitoria ternatea
• Cordyline neocaledonica
• Crambe tatarica
• Diospyros cathayensis
• Diospyros eriantha
• Fritillaria monantha
• Hoffmannia strigillosa
• Humulus lupulus
• Mallotus macrostachyus
• Mallotus metcalfianus
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Primula daonensis
• Pteris semipinnata
• Salvia hispanica
• Scorzonera pseudodivaricata
• Stenocereus griseus
• Styphnolobium japonicum
• Syncarpia hillii
• Tilia miqueliana
• Zea mays

Cross-Links

• PubChem: 5491657
• NPASS: NPC186727
• LOTUS: LTS0203991
• wikiData: Q63393010