2-O-(2-O,6-O-Diacetyl-alpha-D-glucopyranosyl)-1-O-acetyl-3-O-[(E)-3-(4-hydroxyphenyl)acryloyl]-beta-D-fructofuranose

Details

• Internal ID: b8703adc-0af0-4861-8c2c-baa1d6353c5f
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2S,3S,4R,5R)-2-[(2R,3R,4S,5S,6R)-3-acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-2-(acetyloxymethyl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)CO)O)OC(=O)C=CC3=CC=C(C=C3)O)COC(=O)C)OC(=O)C)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)CO)O)OC(=O)/C=C/C3=CC=C(C=C3)O)COC(=O)C)OC(=O)C)O)O
• InChI: InChI=1S/C27H34O16/c1-13(29)37-11-19-21(34)23(36)24(39-15(3)31)26(40-19)43-27(12-38-14(2)30)25(22(35)18(10-28)42-27)41-20(33)9-6-16-4-7-17(32)8-5-16/h4-9,18-19,21-26,28,32,34-36H,10-12H2,1-3H3/b9-6+/t18-,19-,21-,22-,23+,24-,25+,26-,27+/m1/s1
• InChI Key: IUWNEFXWBDZQHK-PZHMIARSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₁₆
• Molecular Weight: 614.50 g/mol
• Exact Mass: 614.18468499 g/mol
• Topological Polar Surface Area (TPSA): 234.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -1.71
• H-Bond Acceptor: 16
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

• 2-O-(2-O,6-O-Diacetyl-alpha-D-glucopyranosyl)-1-O-acetyl-3-O-[(E)-3-(4-hydroxyphenyl)acryloyl]-beta-D-fructofuranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7141	71.41%
Caco-2	-	0.8818	88.18%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7883	78.83%
OATP2B1 inhibitior	-	0.8606	86.06%
OATP1B1 inhibitior	+	0.8095	80.95%
OATP1B3 inhibitior	+	0.9219	92.19%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9032	90.32%
P-glycoprotein inhibitior	+	0.6455	64.55%
P-glycoprotein substrate	-	0.6892	68.92%
CYP3A4 substrate	+	0.6582	65.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8792	87.92%
CYP3A4 inhibition	-	0.8472	84.72%
CYP2C9 inhibition	-	0.8943	89.43%
CYP2C19 inhibition	-	0.9008	90.08%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.8990	89.90%
CYP2C8 inhibition	+	0.7248	72.48%
CYP inhibitory promiscuity	-	0.7794	77.94%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6698	66.98%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9277	92.77%
Skin irritation	-	0.8186	81.86%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3799	37.99%
Micronuclear	-	0.6526	65.26%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8640	86.40%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6331	63.31%
Acute Oral Toxicity (c)	III	0.6006	60.06%
Estrogen receptor binding	+	0.8488	84.88%
Androgen receptor binding	+	0.6449	64.49%
Thyroid receptor binding	+	0.5296	52.96%
Glucocorticoid receptor binding	+	0.6339	63.39%
Aromatase binding	+	0.6173	61.73%
PPAR gamma	+	0.7218	72.18%
Honey bee toxicity	-	0.6815	68.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	0.9533	95.33%

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	98.46%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.52%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.97%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.65%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	91.69%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	91.34%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.01%	94.45%
CHEMBL2996	Q05655	Protein kinase C delta	90.80%	97.79%
CHEMBL2581	P07339	Cathepsin D	89.00%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.30%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.07%	95.56%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.32%	85.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.27%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.00%	97.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	84.53%	93.10%
CHEMBL3194	P02766	Transthyretin	84.05%	90.71%
CHEMBL4040	P28482	MAP kinase ERK2	83.02%	83.82%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.83%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.59%	94.80%
CHEMBL340	P08684	Cytochrome P450 3A4	81.78%	91.19%
CHEMBL4208	P20618	Proteasome component C5	81.61%	90.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.04%	92.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.70%	86.92%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	80.01%	89.67%

Plants that contains it

• Prunus maximowiczii
• Prunus tomentosa

Cross-Links

• PubChem: 14841107
• NPASS: NPC45224
• ChEMBL: CHEMBL3262775
• LOTUS: LTS0039558
• wikiData: Q105120882