[(2R,3S,4R,5R,6S)-3-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-3-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 6825c4d8-6d3e-4011-bcf0-8aec524fd51d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid 3-O-p-coumaroyl glycosides
• IUPAC Name: [(2R,3S,4R,5R,6S)-3-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-3-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)COC(=O)C=CC5=CC=C(C=C5)O)OC6C(C(C(C(O6)CO)OC7C(C(C(C(O7)C)OC8C(C(C(C(O8)CO)O)O)O)O)O)O)O)O)O)C9=CC=C(C=C9)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)/C=C/C5=CC=C(C=C5)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O)O)O)O)C9=CC=C(C=C9)O)O)O)O)O
• InChI: InChI=1S/C54H66O31/c1-18-32(61)35(64)40(69)50(75-18)77-24-13-25(59)31-26(14-24)78-46(21-6-10-23(58)11-7-21)49(34(31)63)85-54-44(73)39(68)48(29(81-54)17-74-30(60)12-5-20-3-8-22(57)9-4-20)84-53-43(72)38(67)47(28(16-56)80-53)83-51-42(71)37(66)45(19(2)76-51)82-52-41(70)36(65)33(62)27(15-55)79-52/h3-14,18-19,27-29,32-33,35-45,47-48,50-59,61-62,64-73H,15-17H2,1-2H3/b12-5+/t18-,19-,27+,28+,29+,32-,33+,35+,36-,37-,38+,39+,40+,41+,42+,43+,44+,45-,47+,48+,50-,51-,52-,53-,54-/m0/s1
• InChI Key: BFKKIBSOJQPWJV-DAXHLPGNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₆₆O₃₁
• Molecular Weight: 1211.10 g/mol
• Exact Mass: 1210.35880530 g/mol
• Topological Polar Surface Area (TPSA): 489.00 Ų
• XlogP: -3.70
• Atomic LogP (AlogP): -5.27
• H-Bond Acceptor: 31
• H-Bond Donor: 17
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5301	53.01%
Caco-2	-	0.8624	86.24%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.6044	60.44%
OATP2B1 inhibitior	-	0.7274	72.74%
OATP1B1 inhibitior	+	0.8719	87.19%
OATP1B3 inhibitior	+	0.9764	97.64%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8358	83.58%
P-glycoprotein inhibitior	+	0.7387	73.87%
P-glycoprotein substrate	+	0.6221	62.21%
CYP3A4 substrate	+	0.6988	69.88%
CYP2C9 substrate	-	0.8173	81.73%
CYP2D6 substrate	-	0.8760	87.60%
CYP3A4 inhibition	-	0.9170	91.70%
CYP2C9 inhibition	-	0.8841	88.41%
CYP2C19 inhibition	-	0.9038	90.38%
CYP2D6 inhibition	-	0.9555	95.55%
CYP1A2 inhibition	-	0.9199	91.99%
CYP2C8 inhibition	+	0.8359	83.59%
CYP inhibitory promiscuity	-	0.7275	72.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6949	69.49%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8984	89.84%
Skin irritation	-	0.8468	84.68%
Skin corrosion	-	0.9526	95.26%
Ames mutagenesis	-	0.5437	54.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7241	72.41%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8902	89.02%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9589	95.89%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.7452	74.52%
Androgen receptor binding	+	0.7030	70.30%
Thyroid receptor binding	+	0.6497	64.97%
Glucocorticoid receptor binding	+	0.7389	73.89%
Aromatase binding	+	0.5676	56.76%
PPAR gamma	+	0.8038	80.38%
Honey bee toxicity	-	0.6600	66.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9464	94.64%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.49%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.48%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	98.93%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.45%	86.33%
CHEMBL2581	P07339	Cathepsin D	96.09%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.50%	96.00%
CHEMBL3194	P02766	Transthyretin	92.58%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	92.45%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.82%	99.17%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.56%	95.64%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.82%	97.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.59%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.49%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.29%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.55%	95.56%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.37%	95.78%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.75%	91.71%
CHEMBL242	Q92731	Estrogen receptor beta	83.30%	98.35%
CHEMBL4208	P20618	Proteasome component C5	83.29%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.01%	85.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.88%	99.15%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.16%	80.78%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.13%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.68%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.37%	90.71%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.35%	94.80%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.33%	95.83%

Plants that contains it

• Koelreuteria paniculata
• Murraya paniculata

Cross-Links

• PubChem: 11968822
• NPASS: NPC223868