[4,5-Dihydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl] 4-hydroxybenzoate

Details

• Internal ID: 7aecd660-ae2c-4050-afd2-bb03ae8248c3
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Hydroxycinnamic acid esters > Coumaric acid esters
• IUPAC Name: [4,5-dihydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl] 4-hydroxybenzoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(OC2OC(=O)C3=CC=C(C=C3)O)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C=CC(=O)OC2C(C(C(OC2OC(=O)C3=CC=C(C=C3)O)COC(=O)C=CC4=CC=C(C=C4)O)O)O)O
• InChI: InChI=1S/C32H30O13/c1-41-24-16-19(4-13-23(24)35)6-15-27(37)44-30-29(39)28(38)25(17-42-26(36)14-5-18-2-9-21(33)10-3-18)43-32(30)45-31(40)20-7-11-22(34)12-8-20/h2-16,25,28-30,32-35,38-39H,17H2,1H3
• InChI Key: LAHQOLQPBYWZMB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₃₀O₁₃
• Molecular Weight: 622.60 g/mol
• Exact Mass: 622.16864101 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 2.30
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5667	56.67%
Caco-2	-	0.8750	87.50%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7752	77.52%
OATP2B1 inhibitior	-	0.7116	71.16%
OATP1B1 inhibitior	+	0.8119	81.19%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8624	86.24%
P-glycoprotein inhibitior	+	0.7285	72.85%
P-glycoprotein substrate	-	0.7225	72.25%
CYP3A4 substrate	+	0.6359	63.59%
CYP2C9 substrate	-	0.6024	60.24%
CYP2D6 substrate	-	0.8473	84.73%
CYP3A4 inhibition	-	0.8799	87.99%
CYP2C9 inhibition	-	0.6518	65.18%
CYP2C19 inhibition	-	0.7100	71.00%
CYP2D6 inhibition	-	0.8994	89.94%
CYP1A2 inhibition	-	0.7425	74.25%
CYP2C8 inhibition	+	0.8695	86.95%
CYP inhibitory promiscuity	-	0.7776	77.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6886	68.86%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9115	91.15%
Skin irritation	-	0.8432	84.32%
Skin corrosion	-	0.9467	94.67%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7042	70.42%
Micronuclear	+	0.6866	68.66%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8866	88.66%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.9667	96.67%
Acute Oral Toxicity (c)	III	0.7241	72.41%
Estrogen receptor binding	+	0.7890	78.90%
Androgen receptor binding	+	0.6093	60.93%
Thyroid receptor binding	+	0.5459	54.59%
Glucocorticoid receptor binding	+	0.6735	67.35%
Aromatase binding	-	0.5879	58.79%
PPAR gamma	+	0.6295	62.95%
Honey bee toxicity	-	0.8359	83.59%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9448	94.48%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.38%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.07%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.53%	96.09%
CHEMBL3194	P02766	Transthyretin	97.52%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	97.37%	91.49%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.22%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.90%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.25%	89.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	92.92%	85.31%
CHEMBL4208	P20618	Proteasome component C5	92.70%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	91.96%	80.78%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	89.36%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.04%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.37%	94.73%
CHEMBL4630	O14757	Serine/threonine-protein kinase Chk1	84.51%	97.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.48%	97.09%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.41%	96.95%
CHEMBL2581	P07339	Cathepsin D	84.16%	98.95%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.96%	95.89%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	83.47%	97.21%
CHEMBL5255	O00206	Toll-like receptor 4	83.41%	92.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.32%	95.89%
CHEMBL2535	P11166	Glucose transporter	80.38%	98.75%

Plants that contains it

• Lycopodium clavatum

Cross-Links

• PubChem: 163019394
• LOTUS: LTS0003448
• wikiData: Q105148648