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

Details

• Internal ID: 22949c7e-4a28-491b-9abc-00078a2c0e6b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 3-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxychromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=C1)OC(=C(C2=O)OC3C(C(C(C(O3)CO)O)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC(=C(C=C5)O)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=C1)OC(=C(C2=O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC(=C(C=C5)O)O)O
• InChI: InChI=1S/C28H32O17/c1-40-10-5-13(33)17-14(6-10)41-24(9-2-3-11(31)12(32)4-9)26(20(17)36)45-28-23(39)25(19(35)16(8-30)43-28)44-27-22(38)21(37)18(34)15(7-29)42-27/h2-6,15-16,18-19,21-23,25,27-35,37-39H,7-8H2,1H3/t15-,16-,18-,19-,21+,22-,23-,25+,27+,28+/m1/s1
• InChI Key: QAKZPBCOTDXPHA-GXUVJXOESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₂O₁₇
• Molecular Weight: 640.50 g/mol
• Exact Mass: 640.16394955 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.41
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5457	54.57%
Caco-2	-	0.9212	92.12%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.5961	59.61%
OATP2B1 inhibitior	-	0.5761	57.61%
OATP1B1 inhibitior	+	0.9253	92.53%
OATP1B3 inhibitior	+	0.9786	97.86%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6857	68.57%
P-glycoprotein inhibitior	-	0.5426	54.26%
P-glycoprotein substrate	-	0.6651	66.51%
CYP3A4 substrate	+	0.6448	64.48%
CYP2C9 substrate	-	0.8415	84.15%
CYP2D6 substrate	-	0.8515	85.15%
CYP3A4 inhibition	-	0.9437	94.37%
CYP2C9 inhibition	-	0.9060	90.60%
CYP2C19 inhibition	-	0.8926	89.26%
CYP2D6 inhibition	-	0.9515	95.15%
CYP1A2 inhibition	-	0.9150	91.50%
CYP2C8 inhibition	+	0.7907	79.07%
CYP inhibitory promiscuity	-	0.7142	71.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.9010	90.10%
Skin irritation	-	0.8320	83.20%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4209	42.09%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.9324	93.24%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8616	86.16%
Acute Oral Toxicity (c)	III	0.6678	66.78%
Estrogen receptor binding	+	0.8413	84.13%
Androgen receptor binding	+	0.7192	71.92%
Thyroid receptor binding	+	0.5626	56.26%
Glucocorticoid receptor binding	+	0.5587	55.87%
Aromatase binding	+	0.5861	58.61%
PPAR gamma	+	0.7471	74.71%
Honey bee toxicity	-	0.7468	74.68%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.6698	66.98%

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%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.39%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.58%	99.15%
CHEMBL2581	P07339	Cathepsin D	95.08%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.07%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.00%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.62%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.53%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.54%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.50%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	91.12%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.60%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	90.34%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.98%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.61%	97.09%
CHEMBL4208	P20618	Proteasome component C5	84.62%	90.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.66%	95.64%

Plants that contains it

• Artemisia lactiflora
• Attalea phalerata
• Catalpa ovata
• Citrus medica
• Crepidiastrum sonchifolium
• Dipsacus inermis
• Duguetia calycina
• Garcinia pyrifera
• Greenwayodendron oliveri
• Jacaranda mimosifolia
• Ophryosporus floribundus
• Payena lucida
• Phalaris canariensis
• Philotheca spicata
• Plumbagella micrantha
• Pteridium aquilinum
• Quassia indica
• Rivina humilis

Cross-Links

• PubChem: 101714010
• NPASS: NPC299822
• LOTUS: LTS0011668
• wikiData: Q105217496