[(2R,3R,4R,5R,6R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5-hydroxy-2-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Details

• Internal ID: 9c9b7881-1e07-424a-87c6-4eeb12a22f51
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [(2R,3R,4R,5R,6R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-5-hydroxy-2-[[(1S,2S,4S,5S,6S,10S)-2-(hydroxymethyl)-10-[(2S,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxan-3-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C3C=COC(C3C4(C2O4)CO)OC5C(C(C(C(O5)CO)O)O)O)OC(=O)C=CC6=CC=C(C=C6)O)OC(=O)C=CC7=CC(=C(C=C7)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H]([C@H]([C@H](O1)O[C@H]2[C@H]3C=CO[C@H]([C@@H]3[C@@]4([C@H]2O4)CO)O[C@H]5[C@H]([C@@H]([C@@H]([C@H](O5)CO)O)O)O)OC(=O)/C=C/C6=CC=C(C=C6)O)OC(=O)/C=C/C7=CC(=C(C=C7)O)O)O
• InChI: InChI=1S/C39H44O19/c1-17-28(47)33(54-25(45)11-6-19-4-9-22(43)23(44)14-19)34(55-26(46)10-5-18-2-7-20(42)8-3-18)38(52-17)56-32-21-12-13-51-36(27(21)39(16-41)35(32)58-39)57-37-31(50)30(49)29(48)24(15-40)53-37/h2-14,17,21,24,27-38,40-44,47-50H,15-16H2,1H3/b10-5+,11-6+/t17-,21+,24-,27-,28-,29-,30-,31+,32+,33-,34-,35+,36+,37+,38-,39-/m1/s1
• InChI Key: CWOWGVARVOJSSH-SFELUPNTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₄O₁₉
• Molecular Weight: 816.80 g/mol
• Exact Mass: 816.24767917 g/mol
• Topological Polar Surface Area (TPSA): 293.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -1.09
• H-Bond Acceptor: 19
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5526	55.26%
Caco-2	-	0.8832	88.32%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.6154	61.54%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8190	81.90%
OATP1B3 inhibitior	+	0.9681	96.81%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7038	70.38%
P-glycoprotein inhibitior	+	0.6778	67.78%
P-glycoprotein substrate	+	0.5618	56.18%
CYP3A4 substrate	+	0.7042	70.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8727	87.27%
CYP3A4 inhibition	-	0.9085	90.85%
CYP2C9 inhibition	-	0.8403	84.03%
CYP2C19 inhibition	-	0.7564	75.64%
CYP2D6 inhibition	-	0.9174	91.74%
CYP1A2 inhibition	-	0.8658	86.58%
CYP2C8 inhibition	+	0.7695	76.95%
CYP inhibitory promiscuity	-	0.7794	77.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5762	57.62%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9078	90.78%
Skin irritation	-	0.7973	79.73%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3786	37.86%
Micronuclear	+	0.6033	60.33%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8010	80.10%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.8067	80.67%
Acute Oral Toxicity (c)	III	0.4971	49.71%
Estrogen receptor binding	+	0.7839	78.39%
Androgen receptor binding	+	0.5905	59.05%
Thyroid receptor binding	+	0.5684	56.84%
Glucocorticoid receptor binding	+	0.6691	66.91%
Aromatase binding	-	0.5056	50.56%
PPAR gamma	+	0.7404	74.04%
Honey bee toxicity	-	0.6691	66.91%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9266	92.66%

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	99.86%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.98%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.03%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.27%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.12%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.03%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.78%	96.00%
CHEMBL3194	P02766	Transthyretin	89.84%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	89.79%	94.73%
CHEMBL2581	P07339	Cathepsin D	89.48%	98.95%
CHEMBL4208	P20618	Proteasome component C5	89.10%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.70%	97.36%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.67%	99.17%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.62%	80.78%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.14%	95.89%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.08%	89.67%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.06%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.24%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.75%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	81.55%	95.93%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	80.86%	97.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.22%	91.07%

Plants that contains it

• Jasminum officinale
• Olea europaea
• Premna odorata
• Syringa vulgaris

Cross-Links

• PubChem: 162821200
• LOTUS: LTS0239686
• wikiData: Q105029987