[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Details

• Internal ID: 92f390a5-8ff7-4453-a3b5-ccfd32b07bae
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC(=C(C=C1CCOC2C(C(C(C(O2)COC(=O)C=CC3=CC(=C(C=C3)O)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1CCO[C@@H]2[C@@H]([C@H]([C@H]([C@H](O2)COC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O[C@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C29H36O16/c30-11-19-22(36)24(38)25(39)29(43-19)45-27-23(37)20(12-42-21(35)6-3-13-1-4-15(31)17(33)9-13)44-28(26(27)40)41-8-7-14-2-5-16(32)18(34)10-14/h1-6,9-10,19-20,22-34,36-40H,7-8,11-12H2/b6-3+/t19-,20+,22-,23-,24+,25-,26+,27-,28-,29-/m0/s1
• InChI Key: CBZYUWGJNYOKHT-VFABPPOMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₆
• Molecular Weight: 640.60 g/mol
• Exact Mass: 640.20033506 g/mol
• Topological Polar Surface Area (TPSA): 266.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -2.04
• H-Bond Acceptor: 16
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7792	77.92%
Caco-2	-	0.9151	91.51%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.7114	71.14%
OATP2B1 inhibitior	-	0.8526	85.26%
OATP1B1 inhibitior	+	0.8736	87.36%
OATP1B3 inhibitior	+	0.9551	95.51%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8148	81.48%
P-glycoprotein inhibitior	-	0.5420	54.20%
P-glycoprotein substrate	-	0.7683	76.83%
CYP3A4 substrate	+	0.6341	63.41%
CYP2C9 substrate	-	0.8024	80.24%
CYP2D6 substrate	-	0.8603	86.03%
CYP3A4 inhibition	-	0.9126	91.26%
CYP2C9 inhibition	-	0.7218	72.18%
CYP2C19 inhibition	-	0.8429	84.29%
CYP2D6 inhibition	-	0.8915	89.15%
CYP1A2 inhibition	-	0.9023	90.23%
CYP2C8 inhibition	+	0.6988	69.88%
CYP inhibitory promiscuity	-	0.7614	76.14%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6808	68.08%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9131	91.31%
Skin irritation	-	0.8373	83.73%
Skin corrosion	-	0.9628	96.28%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6771	67.71%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.9375	93.75%
skin sensitisation	-	0.8107	81.07%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6750	67.50%
Nephrotoxicity	-	0.9103	91.03%
Acute Oral Toxicity (c)	III	0.6718	67.18%
Estrogen receptor binding	+	0.7928	79.28%
Androgen receptor binding	-	0.5095	50.95%
Thyroid receptor binding	+	0.5333	53.33%
Glucocorticoid receptor binding	-	0.5304	53.04%
Aromatase binding	+	0.5774	57.74%
PPAR gamma	+	0.7174	71.74%
Honey bee toxicity	-	0.6725	67.25%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7871	78.71%

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	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.77%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.03%	86.33%
CHEMBL3194	P02766	Transthyretin	95.50%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.89%	96.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.82%	99.17%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.47%	86.92%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.16%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.87%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.65%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.83%	94.73%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.34%	80.78%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	85.75%	96.37%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.84%	94.62%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.26%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	82.83%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.55%	97.09%
CHEMBL2581	P07339	Cathepsin D	81.57%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.40%	96.95%

Plants that contains it

• Plantago major

Cross-Links

• PubChem: 162895889
• LOTUS: LTS0275867
• wikiData: Q104953022