[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 901f6495-0e85-42d1-8f8e-b0e8bf129d31
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6S)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2C(C(C(C(O2)OC3C(C(C(OC3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)OC)CO)O)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O[C@@H]3[C@H]([C@@H]([C@@H](O[C@H]3C4=C(C=C(C5=C4OC(=CC5=O)C6=CC=C(C=C6)O)O)OC)CO)O)O)O)O)O)O
• InChI: InChI=1S/C38H40O18/c1-50-23-11-16(3-9-19(23)41)4-10-27(44)52-15-26-31(46)32(47)34(49)38(55-26)56-37-33(48)30(45)25(14-39)54-36(37)29-24(51-2)13-21(43)28-20(42)12-22(53-35(28)29)17-5-7-18(40)8-6-17/h3-13,25-26,30-34,36-41,43,45-49H,14-15H2,1-2H3/b10-4+/t25-,26+,30+,31+,32-,33-,34+,36-,37+,38-/m0/s1
• InChI Key: NOVNUXFLDIDOCB-XFJYSRFXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₀O₁₈
• Molecular Weight: 784.70 g/mol
• Exact Mass: 784.22146442 g/mol
• Topological Polar Surface Area (TPSA): 281.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 0.20
• H-Bond Acceptor: 18
• H-Bond Donor: 9
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5340	53.40%
Caco-2	-	0.8978	89.78%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9143	91.43%
Subcellular localzation	Mitochondria	0.5166	51.66%
OATP2B1 inhibitior	-	0.5761	57.61%
OATP1B1 inhibitior	+	0.8340	83.40%
OATP1B3 inhibitior	+	0.9824	98.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6853	68.53%
P-glycoprotein inhibitior	+	0.6508	65.08%
P-glycoprotein substrate	+	0.5314	53.14%
CYP3A4 substrate	+	0.6960	69.60%
CYP2C9 substrate	-	0.8152	81.52%
CYP2D6 substrate	-	0.8655	86.55%
CYP3A4 inhibition	-	0.9031	90.31%
CYP2C9 inhibition	-	0.8732	87.32%
CYP2C19 inhibition	-	0.8905	89.05%
CYP2D6 inhibition	-	0.9452	94.52%
CYP1A2 inhibition	-	0.9355	93.55%
CYP2C8 inhibition	+	0.8409	84.09%
CYP inhibitory promiscuity	-	0.7496	74.96%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6813	68.13%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9173	91.73%
Skin irritation	-	0.8436	84.36%
Skin corrosion	-	0.9515	95.15%
Ames mutagenesis	-	0.5829	58.29%
Human Ether-a-go-go-Related Gene inhibition	+	0.7609	76.09%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.8341	83.41%
skin sensitisation	-	0.8927	89.27%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.9018	90.18%
Acute Oral Toxicity (c)	III	0.6240	62.40%
Estrogen receptor binding	+	0.8217	82.17%
Androgen receptor binding	+	0.7829	78.29%
Thyroid receptor binding	+	0.5444	54.44%
Glucocorticoid receptor binding	+	0.6952	69.52%
Aromatase binding	+	0.5795	57.95%
PPAR gamma	+	0.7165	71.65%
Honey bee toxicity	-	0.6607	66.07%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8986	89.86%

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	99.66%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.37%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.88%	89.00%
CHEMBL3194	P02766	Transthyretin	95.31%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.62%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.34%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.03%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.20%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.33%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.77%	94.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.54%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.79%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.51%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.47%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	86.05%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.85%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.62%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	85.20%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.89%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.05%	94.45%
CHEMBL5255	O00206	Toll-like receptor 4	81.49%	92.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.27%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.82%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.73%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.32%	95.83%
CHEMBL242	Q92731	Estrogen receptor beta	80.01%	98.35%

Plants that contains it

• Ziziphus jujuba

Cross-Links

• PubChem: 163105240
• LOTUS: LTS0151854
• wikiData: Q105182833