[(2S,3S,4S,5R)-2-[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 9c94d540-7749-4897-81f4-8ec7357710dc
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3S,4S,5R)-2-[(2R,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• InChI: InChI=1S/C43H46O20/c1-23(45)59-40-38(53)37(52)32(20-44)60-42(40)63-43(22-58-35(50)15-8-24-4-11-27(46)12-5-24)41(54)39(61-36(51)17-10-26-7-14-29(48)31(19-26)56-3)33(62-43)21-57-34(49)16-9-25-6-13-28(47)30(18-25)55-2/h4-19,32-33,37-42,44,46-48,52-54H,20-22H2,1-3H3/b15-8+,16-9+,17-10+/t32-,33-,37-,38+,39-,40-,41+,42-,43+/m1/s1
• InChI Key: LFQJZSMXUJTZON-RJISVSAVSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₃H₄₆O₂₀
• Molecular Weight: 882.80 g/mol
• Exact Mass: 882.25824385 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.10
• H-Bond Acceptor: 20
• H-Bond Donor: 7
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7827	78.27%
Caco-2	-	0.8784	87.84%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7023	70.23%
OATP2B1 inhibitior	-	0.5818	58.18%
OATP1B1 inhibitior	+	0.8071	80.71%
OATP1B3 inhibitior	+	0.9459	94.59%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8774	87.74%
P-glycoprotein inhibitior	+	0.7538	75.38%
P-glycoprotein substrate	-	0.5506	55.06%
CYP3A4 substrate	+	0.6914	69.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.7802	78.02%
CYP2C9 inhibition	-	0.8269	82.69%
CYP2C19 inhibition	-	0.8158	81.58%
CYP2D6 inhibition	-	0.9296	92.96%
CYP1A2 inhibition	-	0.8796	87.96%
CYP2C8 inhibition	+	0.8015	80.15%
CYP inhibitory promiscuity	-	0.7421	74.21%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6433	64.33%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9095	90.95%
Skin irritation	-	0.8527	85.27%
Skin corrosion	-	0.9546	95.46%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8202	82.02%
Micronuclear	-	0.5426	54.26%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8251	82.51%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.8323	83.23%
Acute Oral Toxicity (c)	III	0.6316	63.16%
Estrogen receptor binding	+	0.8391	83.91%
Androgen receptor binding	+	0.7049	70.49%
Thyroid receptor binding	+	0.6116	61.16%
Glucocorticoid receptor binding	+	0.6720	67.20%
Aromatase binding	+	0.5580	55.80%
PPAR gamma	+	0.7542	75.42%
Honey bee toxicity	-	0.6643	66.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.9374	93.74%

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	99.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.44%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.36%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.87%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.49%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.76%	94.45%
CHEMBL3194	P02766	Transthyretin	93.54%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.13%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.69%	99.17%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.60%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	88.34%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.87%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.21%	89.62%
CHEMBL1951	P21397	Monoamine oxidase A	84.66%	91.49%
CHEMBL340	P08684	Cytochrome P450 3A4	84.43%	91.19%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.37%	85.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.92%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.09%	97.09%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	82.90%	97.03%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	82.83%	89.44%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.26%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.09%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	82.05%	95.93%
CHEMBL5255	O00206	Toll-like receptor 4	81.77%	92.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.48%	94.08%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.60%	93.10%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	80.24%	80.78%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.16%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.16%	99.15%

Plants that contains it

• Smilax bracteata

Cross-Links

• PubChem: 163049694
• LOTUS: LTS0036978
• wikiData: Q105151127