[(2R,3R,4S,5S)-5-(acetyloxymethyl)-5-[(2R,3R,4S,5S,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-hydroxyoxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: d311bbbb-96f9-4f71-9ffe-26cef7185538
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Hexacarboxylic acids and derivatives
• IUPAC Name: [(2R,3R,4S,5S)-5-(acetyloxymethyl)-5-[(2R,3R,4S,5S,6R)-3,5-diacetyloxy-6-(acetyloxymethyl)-4-hydroxyoxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxyoxolan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)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)OC)O)OC(=O)C=CC4=CC(=C(C=C4)O)OC)COC(=O)C)OC(=O)C)O)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)OC)O)OC(=O)/C=C/C4=CC(=C(C=C4)O)OC)COC(=O)C)OC(=O)C)O)OC(=O)C
• InChI: InChI=1S/C40H46O21/c1-20(41)53-18-31-36(56-22(3)43)35(50)37(57-23(4)44)39(58-31)61-40(19-55-21(2)42)38(59-33(48)14-10-25-8-12-27(46)29(16-25)52-6)34(49)30(60-40)17-54-32(47)13-9-24-7-11-26(45)28(15-24)51-5/h7-16,30-31,34-39,45-46,49-50H,17-19H2,1-6H3/b13-9+,14-10+/t30-,31-,34-,35+,36-,37-,38+,39-,40+/m1/s1
• InChI Key: OGAPXYQOTIOKDV-RODZTRATSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₄₆O₂₁
• Molecular Weight: 862.80 g/mol
• Exact Mass: 862.25315847 g/mol
• Topological Polar Surface Area (TPSA): 285.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 0.84
• H-Bond Acceptor: 21
• H-Bond Donor: 4
• Rotatable Bonds: 17

Synonyms

• 1-O-Acetyl-3-O,6-O-bis[3-(4-hydroxy-3-methoxyphenyl)acryloyl]-beta-D-fructofuranosyl 2-O,4-O,6-O-triacetyl-alpha-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7432	74.32%
Caco-2	-	0.8675	86.75%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8081	80.81%
OATP2B1 inhibitior	-	0.5787	57.87%
OATP1B1 inhibitior	+	0.8531	85.31%
OATP1B3 inhibitior	+	0.8876	88.76%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9464	94.64%
P-glycoprotein inhibitior	+	0.7812	78.12%
P-glycoprotein substrate	-	0.6103	61.03%
CYP3A4 substrate	+	0.6687	66.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8697	86.97%
CYP3A4 inhibition	-	0.8368	83.68%
CYP2C9 inhibition	-	0.7349	73.49%
CYP2C19 inhibition	-	0.7377	73.77%
CYP2D6 inhibition	-	0.9229	92.29%
CYP1A2 inhibition	-	0.8214	82.14%
CYP2C8 inhibition	+	0.7845	78.45%
CYP inhibitory promiscuity	-	0.6384	63.84%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9528	95.28%
Carcinogenicity (trinary)	Non-required	0.6239	62.39%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9097	90.97%
Skin irritation	-	0.8556	85.56%
Skin corrosion	-	0.9591	95.91%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7117	71.17%
Micronuclear	-	0.5452	54.52%
Hepatotoxicity	-	0.9125	91.25%
skin sensitisation	-	0.8235	82.35%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8048	80.48%
Acute Oral Toxicity (c)	III	0.4921	49.21%
Estrogen receptor binding	+	0.8484	84.84%
Androgen receptor binding	+	0.7162	71.62%
Thyroid receptor binding	+	0.6405	64.05%
Glucocorticoid receptor binding	+	0.7468	74.68%
Aromatase binding	+	0.5886	58.86%
PPAR gamma	+	0.7748	77.48%
Honey bee toxicity	-	0.7141	71.41%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5255	52.55%
Fish aquatic toxicity	+	0.9825	98.25%

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	99.65%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.76%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.64%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.22%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.27%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.33%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	92.24%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.52%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.39%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.32%	85.14%
CHEMBL3194	P02766	Transthyretin	91.30%	90.71%
CHEMBL4208	P20618	Proteasome component C5	90.98%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.46%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.12%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.39%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	84.39%	91.19%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.72%	97.36%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.20%	89.62%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.02%	97.21%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.52%	96.95%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.12%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.86%	98.95%

Plants that contains it

• Hypericum sampsonii
• Hypericum scabrum
• Polygonum perfoliatum

Cross-Links

• PubChem: 10748170
• NPASS: NPC290561
• LOTUS: LTS0071452
• wikiData: Q27138667