2-[4-[6-O-(3,5-Dimethoxy-4-hydroxycinnamoyl)-beta-D-glucopyranosyloxy]phenyl]-5-hydroxy-6-(beta-D-glucopyranosyl)-7-(3,5-dimethoxy-4-hydroxycinnamoyloxy)-4H-1-benzopyran-4-one

Details

• Internal ID: 63b4b011-1f11-4952-bec1-3e23aaf4d6fa
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[4-[5-hydroxy-7-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy-4-oxo-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-2-yl]phenoxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=CC(=CC(=C1O)OC)C=CC(=O)OCC2C(C(C(C(O2)OC3=CC=C(C=C3)C4=CC(=O)C5=C(C(=C(C=C5O4)OC(=O)C=CC6=CC(=C(C(=C6)OC)O)OC)C7C(C(C(C(O7)CO)O)O)O)O)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)OC)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC=C(C=C3)C4=CC(=O)C5=C(C(=C(C=C5O4)OC(=O)/C=C/C6=CC(=C(C(=C6)OC)O)OC)[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)O
• InChI: InChI=1S/C49H50O23/c1-63-29-13-21(14-30(64-2)39(29)54)5-11-35(52)67-20-34-42(57)45(60)47(62)49(72-34)68-24-9-7-23(8-10-24)26-17-25(51)37-27(69-26)18-28(38(43(37)58)48-46(61)44(59)41(56)33(19-50)71-48)70-36(53)12-6-22-15-31(65-3)40(55)32(16-22)66-4/h5-18,33-34,41-42,44-50,54-62H,19-20H2,1-4H3/b11-5+,12-6+/t33-,34-,41-,42-,44+,45+,46-,47-,48+,49-/m1/s1
• InChI Key: KALHUUXNMGAUKH-OTKSHJOWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₉H₅₀O₂₃
• Molecular Weight: 1006.90 g/mol
• Exact Mass: 1006.27428784 g/mol
• Topological Polar Surface Area (TPSA): 346.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 23
• H-Bond Donor: 10
• Rotatable Bonds: 16

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5284	52.84%
Caco-2	-	0.8617	86.17%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.4963	49.63%
OATP2B1 inhibitior	-	0.5716	57.16%
OATP1B1 inhibitior	+	0.8008	80.08%
OATP1B3 inhibitior	+	0.9721	97.21%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9162	91.62%
P-glycoprotein inhibitior	+	0.7464	74.64%
P-glycoprotein substrate	+	0.5754	57.54%
CYP3A4 substrate	+	0.6901	69.01%
CYP2C9 substrate	-	0.8152	81.52%
CYP2D6 substrate	-	0.8655	86.55%
CYP3A4 inhibition	-	0.9320	93.20%
CYP2C9 inhibition	-	0.8977	89.77%
CYP2C19 inhibition	-	0.9209	92.09%
CYP2D6 inhibition	-	0.9517	95.17%
CYP1A2 inhibition	-	0.9398	93.98%
CYP2C8 inhibition	+	0.8320	83.20%
CYP inhibitory promiscuity	-	0.7831	78.31%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6541	65.41%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8990	89.90%
Skin irritation	-	0.8479	84.79%
Skin corrosion	-	0.9548	95.48%
Ames mutagenesis	-	0.5465	54.65%
Human Ether-a-go-go-Related Gene inhibition	+	0.7643	76.43%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8995	89.95%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.9431	94.31%
Acute Oral Toxicity (c)	III	0.6211	62.11%
Estrogen receptor binding	+	0.7735	77.35%
Androgen receptor binding	+	0.7349	73.49%
Thyroid receptor binding	+	0.5978	59.78%
Glucocorticoid receptor binding	+	0.6640	66.40%
Aromatase binding	+	0.6179	61.79%
PPAR gamma	+	0.7521	75.21%
Honey bee toxicity	-	0.6381	63.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9012	90.12%

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	99.69%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.19%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.60%	96.00%
CHEMBL2581	P07339	Cathepsin D	96.49%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.44%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.80%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.37%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.21%	85.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.85%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.35%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.62%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.30%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	87.34%	94.73%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.79%	96.21%
CHEMBL3194	P02766	Transthyretin	85.13%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.05%	95.89%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	81.59%	83.57%
CHEMBL220	P22303	Acetylcholinesterase	81.06%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.46%	90.71%

Plants that contains it

• Chrysosplenium americanum
• Eriocapitella tomentosa
• Eritrichium sericeum
• Eutrema japonicum
• Olea europaea
• Phlogacanthus tubiflorus
• Sabia japonica
• Woodsia manchuriensis

Cross-Links

• PubChem: 102352342
• NPASS: NPC265148
• LOTUS: LTS0271973
• wikiData: Q105137890