[2-[3-Acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-5-(acetyloxymethyl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: ba6f96c8-b0c4-4d7a-a47f-8fcd5a2d832d
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [2-[3-acetyloxy-6-(acetyloxymethyl)-4,5-dihydroxyoxan-2-yl]oxy-5-(acetyloxymethyl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] 3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C)O)OC(=O)C=CC3=CC=C(C=C3)O)CO)OC(=O)C)O)O
• SMILES (Isomeric): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C)O)OC(=O)C=CC3=CC=C(C=C3)O)CO)OC(=O)C)O)O
• InChI: InChI=1S/C27H34O16/c1-13(29)37-10-18-21(34)23(36)24(39-15(3)31)26(40-18)43-27(12-28)25(22(35)19(42-27)11-38-14(2)30)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
• InChI Key: OYHUIOMLUYPLSY-UHFFFAOYSA-N
• Popularity: 0 references 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: -1.50
• Atomic LogP (AlogP): -1.71
• H-Bond Acceptor: 16
• H-Bond Donor: 5
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4846	48.46%
Caco-2	-	0.8743	87.43%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.8470	84.70%
OATP2B1 inhibitior	-	0.8611	86.11%
OATP1B1 inhibitior	+	0.8225	82.25%
OATP1B3 inhibitior	+	0.8966	89.66%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8921	89.21%
P-glycoprotein inhibitior	+	0.6493	64.93%
P-glycoprotein substrate	-	0.7230	72.30%
CYP3A4 substrate	+	0.6536	65.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8792	87.92%
CYP3A4 inhibition	-	0.8307	83.07%
CYP2C9 inhibition	-	0.8806	88.06%
CYP2C19 inhibition	-	0.8761	87.61%
CYP2D6 inhibition	-	0.9387	93.87%
CYP1A2 inhibition	-	0.8693	86.93%
CYP2C8 inhibition	+	0.6963	69.63%
CYP inhibitory promiscuity	-	0.7924	79.24%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6412	64.12%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9285	92.85%
Skin irritation	-	0.8203	82.03%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7105	71.05%
Micronuclear	-	0.6426	64.26%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8609	86.09%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6834	68.34%
Acute Oral Toxicity (c)	III	0.5918	59.18%
Estrogen receptor binding	+	0.8275	82.75%
Androgen receptor binding	+	0.6199	61.99%
Thyroid receptor binding	+	0.5253	52.53%
Glucocorticoid receptor binding	+	0.6175	61.75%
Aromatase binding	+	0.5732	57.32%
PPAR gamma	+	0.7039	70.39%
Honey bee toxicity	-	0.7375	73.75%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9625	96.25%

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	98.49%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.48%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.88%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.54%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	91.95%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.33%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.74%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.07%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.07%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.28%	85.14%
CHEMBL2996	Q05655	Protein kinase C delta	85.78%	97.79%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.79%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.57%	85.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.26%	95.50%
CHEMBL3194	P02766	Transthyretin	84.05%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	83.82%	91.49%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.45%	89.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.28%	97.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.51%	93.10%
CHEMBL5255	O00206	Toll-like receptor 4	81.42%	92.50%

Plants that contains it

• Prunus maximowiczii

Cross-Links

• PubChem: 163078665
• LOTUS: LTS0166053
• wikiData: Q105203312