(2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: 9841be3a-a23e-4bfd-a945-41ea4f5ee59c
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C2=CC(=O)C3=C(C=C(C=C3O2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)O)O
• InChI: InChI=1S/C28H30O17/c1-40-15-4-9(2-3-11(15)30)14-7-13(32)18-12(31)5-10(6-16(18)42-14)41-28-25(21(35)19(33)17(8-29)43-28)45-27-23(37)20(34)22(36)24(44-27)26(38)39/h2-7,17,19-25,27-31,33-37H,8H2,1H3,(H,38,39)/t17-,19-,20+,21+,22+,23-,24+,25-,27+,28-/m1/s1
• InChI Key: PNHGTHGNROOTDD-NDAVQDCPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₀O₁₇
• Molecular Weight: 638.50 g/mol
• Exact Mass: 638.14829948 g/mol
• Topological Polar Surface Area (TPSA): 272.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): -2.02
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• 2-(3-Methoxy-4-hydroxyphenyl)-5-hydroxy-7-[2-O-(beta-D-glucopyranuronosyl)-beta-D-glucopyranosyloxy]-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5915	59.15%
Caco-2	-	0.9169	91.69%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5769	57.69%
OATP2B1 inhibitior	-	0.7040	70.40%
OATP1B1 inhibitior	+	0.9240	92.40%
OATP1B3 inhibitior	+	0.9835	98.35%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5300	53.00%
P-glycoprotein inhibitior	-	0.5503	55.03%
P-glycoprotein substrate	-	0.6196	61.96%
CYP3A4 substrate	+	0.6381	63.81%
CYP2C9 substrate	-	0.8216	82.16%
CYP2D6 substrate	-	0.8726	87.26%
CYP3A4 inhibition	-	0.9170	91.70%
CYP2C9 inhibition	-	0.8902	89.02%
CYP2C19 inhibition	-	0.9278	92.78%
CYP2D6 inhibition	-	0.9639	96.39%
CYP1A2 inhibition	-	0.9238	92.38%
CYP2C8 inhibition	+	0.8125	81.25%
CYP inhibitory promiscuity	-	0.8531	85.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6954	69.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9187	91.87%
Skin irritation	-	0.8345	83.45%
Skin corrosion	-	0.9551	95.51%
Ames mutagenesis	-	0.5364	53.64%
Human Ether-a-go-go-Related Gene inhibition	+	0.7415	74.15%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8841	88.41%
skin sensitisation	-	0.9384	93.84%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.9291	92.91%
Acute Oral Toxicity (c)	III	0.6154	61.54%
Estrogen receptor binding	+	0.8253	82.53%
Androgen receptor binding	+	0.6014	60.14%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5915	59.15%
Aromatase binding	+	0.6078	60.78%
PPAR gamma	+	0.7316	73.16%
Honey bee toxicity	-	0.6851	68.51%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.7782	77.82%

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	99.27%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	95.86%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.76%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.88%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.18%	85.14%
CHEMBL2581	P07339	Cathepsin D	94.10%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.80%	86.33%
CHEMBL3194	P02766	Transthyretin	93.66%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.10%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.87%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.05%	99.17%
CHEMBL220	P22303	Acetylcholinesterase	91.23%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.77%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.74%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.01%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.17%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.74%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.61%	96.00%
CHEMBL3401	O75469	Pregnane X receptor	84.47%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.61%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.36%	95.89%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	81.14%	95.48%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.97%	95.78%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.69%	90.71%

Plants that contains it

• Elsholtzia ciliata
• Stratiotes aloides

Cross-Links

• PubChem: 44139739
• NPASS: NPC270592
• LOTUS: LTS0223778
• wikiData: Q105211931