[(2S,3S,4R,5R)-5-(acetyloxymethyl)-2-[(2R,3R,4S,5S,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-hydroxyoxan-2-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 32df0d76-b1db-4acc-928a-ce26924917f9
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2S,3S,4R,5R)-5-(acetyloxymethyl)-2-[(2R,3R,4S,5S,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-hydroxyoxan-2-yl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(O1)(CO)OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)O)OC(=O)C)OC(=O)C=CC3=CC=C(C=C3)O)O
• SMILES (Isomeric): CC(=O)OC[C@@H]1[C@H]([C@@H]([C@](O1)(CO)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)O)OC(=O)C)OC(=O)/C=C/C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C29H36O17/c1-14(31)39-11-20-23(37)27(44-22(36)10-7-18-5-8-19(35)9-6-18)29(13-30,45-20)46-28-26(42-17(4)34)24(38)25(41-16(3)33)21(43-28)12-40-15(2)32/h5-10,20-21,23-28,30,35,37-38H,11-13H2,1-4H3/b10-7+/t20-,21-,23-,24+,25-,26-,27+,28-,29+/m1/s1
• InChI Key: XWPPRVNDLPFLQI-VAVFHNSSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₇
• Molecular Weight: 656.60 g/mol
• Exact Mass: 656.19524968 g/mol
• Topological Polar Surface Area (TPSA): 240.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.14
• H-Bond Acceptor: 17
• H-Bond Donor: 4
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6950	69.50%
Caco-2	-	0.8676	86.76%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8405	84.05%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8344	83.44%
OATP1B3 inhibitior	+	0.8725	87.25%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8931	89.31%
P-glycoprotein inhibitior	+	0.7401	74.01%
P-glycoprotein substrate	-	0.7025	70.25%
CYP3A4 substrate	+	0.6575	65.75%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.7770	77.70%
CYP2C9 inhibition	-	0.8638	86.38%
CYP2C19 inhibition	-	0.8659	86.59%
CYP2D6 inhibition	-	0.9382	93.82%
CYP1A2 inhibition	-	0.8792	87.92%
CYP2C8 inhibition	+	0.7112	71.12%
CYP inhibitory promiscuity	-	0.6475	64.75%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9428	94.28%
Carcinogenicity (trinary)	Non-required	0.6159	61.59%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9199	91.99%
Skin irritation	-	0.8217	82.17%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7154	71.54%
Micronuclear	-	0.6726	67.26%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8603	86.03%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.4731	47.31%
Acute Oral Toxicity (c)	III	0.5419	54.19%
Estrogen receptor binding	+	0.8224	82.24%
Androgen receptor binding	+	0.6293	62.93%
Thyroid receptor binding	+	0.5446	54.46%
Glucocorticoid receptor binding	+	0.6443	64.43%
Aromatase binding	+	0.5964	59.64%
PPAR gamma	+	0.7135	71.35%
Honey bee toxicity	-	0.7446	74.46%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9571	95.71%

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	98.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	93.48%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.10%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.85%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	91.08%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.64%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.69%	96.00%
CHEMBL2581	P07339	Cathepsin D	87.59%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.51%	95.56%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.35%	89.67%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.79%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	85.40%	91.49%
CHEMBL2996	Q05655	Protein kinase C delta	84.46%	97.79%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.36%	85.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.17%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.64%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.81%	97.09%
CHEMBL3194	P02766	Transthyretin	82.68%	90.71%
CHEMBL4208	P20618	Proteasome component C5	82.16%	90.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.15%	92.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.61%	91.19%

Plants that contains it

• Prunus maximowiczii

Cross-Links

• PubChem: 14841105
• LOTUS: LTS0078700
• wikiData: Q105343700