[(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-hydroxy-4-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: fcee719c-a58a-40b6-be14-cc34d90532de
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-hydroxy-4-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]methoxy]oxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)COC2C(C(OC(C2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)COC(=O)C=CC4=CC(=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)CO[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2OC(=O)C)OCCC3=CC(=C(C=C3)O)O)COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C32H40O16/c1-15-26(39)29(42)27(40)23(46-15)14-45-30-28(41)24(13-44-25(38)8-5-17-3-6-19(34)21(36)11-17)48-32(31(30)47-16(2)33)43-10-9-18-4-7-20(35)22(37)12-18/h3-8,11-12,15,23-24,26-32,34-37,39-42H,9-10,13-14H2,1-2H3/b8-5+/t15-,23-,24+,26-,27-,28+,29+,30-,31+,32+/m0/s1
• InChI Key: OSOFNYSIWGSNBA-BORBUMKPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀O₁₆
• Molecular Weight: 680.60 g/mol
• Exact Mass: 680.23163518 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.40
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.8273	82.73%
Caco-2	-	0.8923	89.23%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7983	79.83%
OATP2B1 inhibitior	-	0.7240	72.40%
OATP1B1 inhibitior	+	0.8536	85.36%
OATP1B3 inhibitior	+	0.9206	92.06%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9019	90.19%
P-glycoprotein inhibitior	+	0.6010	60.10%
P-glycoprotein substrate	-	0.6223	62.23%
CYP3A4 substrate	+	0.6524	65.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8751	87.51%
CYP3A4 inhibition	-	0.8785	87.85%
CYP2C9 inhibition	-	0.6449	64.49%
CYP2C19 inhibition	-	0.8274	82.74%
CYP2D6 inhibition	-	0.9282	92.82%
CYP1A2 inhibition	-	0.8025	80.25%
CYP2C8 inhibition	+	0.6960	69.60%
CYP inhibitory promiscuity	-	0.8019	80.19%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6797	67.97%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9213	92.13%
Skin irritation	-	0.8486	84.86%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3684	36.84%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.8551	85.51%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.9383	93.83%
Acute Oral Toxicity (c)	III	0.7732	77.32%
Estrogen receptor binding	+	0.7988	79.88%
Androgen receptor binding	-	0.6383	63.83%
Thyroid receptor binding	+	0.5267	52.67%
Glucocorticoid receptor binding	+	0.6389	63.89%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.7312	73.12%
Honey bee toxicity	-	0.7143	71.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9373	93.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.56%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.21%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.14%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	94.57%	94.73%
CHEMBL2581	P07339	Cathepsin D	94.30%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.43%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.31%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.01%	99.17%
CHEMBL3194	P02766	Transthyretin	91.34%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.46%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	90.27%	95.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.65%	96.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	85.05%	94.80%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.36%	95.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	83.35%	86.92%
CHEMBL4208	P20618	Proteasome component C5	82.98%	90.00%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	82.81%	96.37%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.11%	80.78%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.74%	95.89%

Plants that contains it

• Cistanche deserticola
• Cistanche phelypaea

Cross-Links

• PubChem: 46228758
• NPASS: NPC47471
• ChEMBL: CHEMBL590315
• LOTUS: LTS0082673
• wikiData: Q105199136