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

Details

• Internal ID: 43c73f16-ef17-4d74-a65b-c1f53df761c9
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2R,3R,4S,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-3,5-dihydroxy-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2O)OCCC3=CC(=C(C=C3)O)O)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H]([C@H](O[C@H]([C@@H]2O)OCCC3=CC(=C(C=C3)O)O)COC(=O)/C=C/C4=CC=C(C=C4)O)O)O)O)O
• InChI: InChI=1S/C29H36O14/c1-14-22(34)24(36)25(37)29(41-14)43-27-23(35)20(13-40-21(33)9-5-15-2-6-17(30)7-3-15)42-28(26(27)38)39-11-10-16-4-8-18(31)19(32)12-16/h2-9,12,14,20,22-32,34-38H,10-11,13H2,1H3/b9-5+/t14-,20+,22-,23+,24+,25+,26+,27-,28+,29-/m0/s1
• InChI Key: NPUWOLLECFYVQL-AQFWLZLQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₄
• Molecular Weight: 608.60 g/mol
• Exact Mass: 608.21050582 g/mol
• Topological Polar Surface Area (TPSA): 225.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.72
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7283	72.83%
Caco-2	-	0.9133	91.33%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.8183	81.83%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.8811	88.11%
OATP1B3 inhibitior	+	0.9490	94.90%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7793	77.93%
P-glycoprotein inhibitior	-	0.6327	63.27%
P-glycoprotein substrate	-	0.5905	59.05%
CYP3A4 substrate	+	0.6604	66.04%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8696	86.96%
CYP3A4 inhibition	-	0.9284	92.84%
CYP2C9 inhibition	-	0.7093	70.93%
CYP2C19 inhibition	-	0.8036	80.36%
CYP2D6 inhibition	-	0.8975	89.75%
CYP1A2 inhibition	-	0.8055	80.55%
CYP2C8 inhibition	+	0.7756	77.56%
CYP inhibitory promiscuity	-	0.6658	66.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6280	62.80%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9247	92.47%
Skin irritation	-	0.8390	83.90%
Skin corrosion	-	0.9508	95.08%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3984	39.84%
Micronuclear	-	0.6367	63.67%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8344	83.44%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.9252	92.52%
Acute Oral Toxicity (c)	III	0.7807	78.07%
Estrogen receptor binding	+	0.7584	75.84%
Androgen receptor binding	+	0.5459	54.59%
Thyroid receptor binding	+	0.5265	52.65%
Glucocorticoid receptor binding	-	0.4638	46.38%
Aromatase binding	-	0.4831	48.31%
PPAR gamma	+	0.6935	69.35%
Honey bee toxicity	-	0.6862	68.62%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.8812	88.12%

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	99.41%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.90%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.51%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.20%	96.09%
CHEMBL3194	P02766	Transthyretin	94.95%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.37%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.39%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	92.94%	94.73%
CHEMBL2581	P07339	Cathepsin D	90.14%	98.95%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.71%	96.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.21%	89.67%
CHEMBL226	P30542	Adenosine A1 receptor	85.72%	95.93%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	85.72%	80.78%
CHEMBL4208	P20618	Proteasome component C5	85.16%	90.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.86%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.71%	86.92%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.02%	90.71%
CHEMBL2179	P04062	Beta-glucocerebrosidase	82.97%	85.31%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.13%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.04%	97.36%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.64%	91.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.14%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	80.16%	85.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.10%	95.56%

Plants that contains it

• Ligustrum pricei

Cross-Links

• PubChem: 101666176
• LOTUS: LTS0054301
• wikiData: Q105183448