3-O-[4-Hydroxy-trans-cinnamoyl]-1-O-acetyl-beta-D-fructofuranosyl 3-O,6-O-diacetyl alpha-D-glucopyranoside

Details

• Internal ID: 41e9722a-f2ab-4380-b18d-646d8896f26b
• 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,5R,6R)-4-acetyloxy-6-(acetyloxymethyl)-3,5-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)O)OC(=O)C)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)O)OC(=O)C)O
• InChI: InChI=1S/C27H34O16/c1-13(29)37-11-19-21(34)24(39-15(3)31)23(36)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: MTCNFFCDPXLWCX-HBDYSYHISA-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

• 3-O-[4-Hydroxy-trans-cinnamoyl]-1-O-acetyl-beta-D-fructofuranosyl 3-O,6-O-diacetyl alpha-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5322	53.22%
Caco-2	-	0.8819	88.19%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7742	77.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8341	83.41%
OATP1B3 inhibitior	+	0.9024	90.24%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9152	91.52%
P-glycoprotein inhibitior	+	0.6522	65.22%
P-glycoprotein substrate	-	0.6592	65.92%
CYP3A4 substrate	+	0.6664	66.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.7829	78.29%
CYP2C9 inhibition	-	0.8721	87.21%
CYP2C19 inhibition	-	0.8851	88.51%
CYP2D6 inhibition	-	0.9344	93.44%
CYP1A2 inhibition	-	0.9014	90.14%
CYP2C8 inhibition	+	0.7235	72.35%
CYP inhibitory promiscuity	-	0.6265	62.65%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9628	96.28%
Carcinogenicity (trinary)	Non-required	0.6507	65.07%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9235	92.35%
Skin irritation	-	0.8184	81.84%
Skin corrosion	-	0.9567	95.67%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6686	66.86%
Micronuclear	-	0.6726	67.26%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8628	86.28%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6084	60.84%
Acute Oral Toxicity (c)	III	0.5565	55.65%
Estrogen receptor binding	+	0.8587	85.87%
Androgen receptor binding	+	0.6461	64.61%
Thyroid receptor binding	+	0.5467	54.67%
Glucocorticoid receptor binding	+	0.6683	66.83%
Aromatase binding	+	0.6409	64.09%
PPAR gamma	+	0.7044	70.44%
Honey bee toxicity	-	0.6658	66.58%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9466	94.66%

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	98.68%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.90%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.19%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.50%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.28%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.05%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.85%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.89%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.83%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.62%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	86.34%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.95%	97.09%
CHEMBL2581	P07339	Cathepsin D	84.66%	98.95%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	84.65%	89.67%
CHEMBL340	P08684	Cytochrome P450 3A4	84.27%	91.19%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.00%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.61%	99.17%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	83.14%	94.80%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.92%	85.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.51%	97.79%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.29%	93.10%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.85%	97.28%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.52%	95.89%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.29%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	80.22%	91.49%

Plants that contains it

• Prunus padus
• Prunus tomentosa

Cross-Links

• PubChem: 21629983
• NPASS: NPC35288
• ChEMBL: CHEMBL3262774
• LOTUS: LTS0269190
• wikiData: Q105171613