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

Details

• Internal ID: 6c37bbe1-ac11-4596-bb82-3af6332afc09
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: [(2R,3S,4S,5S)-5-(acetyloxymethyl)-5-[(2R,3R,4R,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-hydroxyoxan-2-yl]oxy-3,4-dihydroxyoxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C=CC3=CC=C(C=C3)O)O)O)COC(=O)C)O)OC(=O)C)OC(=O)C
• 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)COC(=O)/C=C/C3=CC=C(C=C3)O)O)O)COC(=O)C)O)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C29H36O17/c1-14(30)39-12-21-25(42-16(3)32)26(43-17(4)33)24(37)28(44-21)46-29(13-41-15(2)31)27(38)23(36)20(45-29)11-40-22(35)10-7-18-5-8-19(34)9-6-18/h5-10,20-21,23-28,34,36-38H,11-13H2,1-4H3/b10-7+/t20-,21-,23-,24-,25-,26-,27+,28-,29+/m1/s1
• InChI Key: TWXLNQHRCVWVAT-VZOQTWIESA-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	+	0.5701	57.01%
Caco-2	-	0.8672	86.72%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.8654	86.54%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.8261	82.61%
OATP1B3 inhibitior	+	0.8706	87.06%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8693	86.93%
P-glycoprotein inhibitior	+	0.7252	72.52%
P-glycoprotein substrate	-	0.6952	69.52%
CYP3A4 substrate	+	0.6691	66.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8803	88.03%
CYP3A4 inhibition	-	0.8840	88.40%
CYP2C9 inhibition	-	0.8471	84.71%
CYP2C19 inhibition	-	0.8523	85.23%
CYP2D6 inhibition	-	0.9382	93.82%
CYP1A2 inhibition	-	0.8544	85.44%
CYP2C8 inhibition	+	0.6800	68.00%
CYP inhibitory promiscuity	-	0.7768	77.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6158	61.58%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9183	91.83%
Skin irritation	-	0.8171	81.71%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4802	48.02%
Micronuclear	-	0.6052	60.52%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8466	84.66%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7091	70.91%
Acute Oral Toxicity (c)	III	0.6021	60.21%
Estrogen receptor binding	+	0.8178	81.78%
Androgen receptor binding	+	0.6649	66.49%
Thyroid receptor binding	+	0.5640	56.40%
Glucocorticoid receptor binding	+	0.7097	70.97%
Aromatase binding	+	0.6466	64.66%
PPAR gamma	+	0.7254	72.54%
Honey bee toxicity	-	0.6936	69.36%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9795	97.95%

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	98.32%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.42%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.12%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.56%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	93.08%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.67%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.31%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	90.98%	95.93%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	90.38%	89.67%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.00%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.93%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.32%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.23%	99.17%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.11%	97.28%
CHEMBL2581	P07339	Cathepsin D	82.59%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.58%	97.09%
CHEMBL4208	P20618	Proteasome component C5	81.42%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.22%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.95%	85.00%

Plants that contains it

• Prunus mume

Cross-Links

• PubChem: 21592299
• NPASS: NPC242773
• LOTUS: LTS0123256
• wikiData: Q105266192