[2-[[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl] 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: 1676287e-8941-43ee-a2a6-5fa9049831be
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [2-[[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxymethyl]-6-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-3-yl] 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CC(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)OC)COC4C(C(CO4)(CO)O)O)OCCC5=CC(=C(C=C5)OC)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2CC(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)OC)COC4C(C(CO4)(CO)O)O)OCCC5=CC(=C(C=C5)OC)O)O)O)O
• InChI: InChI=1S/C36H48O18/c1-18-29(41)30(42)31(43)34(51-18)53-25-14-28(48-11-10-20-5-8-23(46-2)22(39)12-20)52-26(15-49-35-33(44)36(45,16-37)17-50-35)32(25)54-27(40)9-6-19-4-7-21(38)24(13-19)47-3/h4-9,12-13,18,25-26,28-35,37-39,41-45H,10-11,14-17H2,1-3H3
• InChI Key: TYKWSXKLDHLLAB-UHFFFAOYSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₈O₁₈
• Molecular Weight: 768.80 g/mol
• Exact Mass: 768.28406468 g/mol
• Topological Polar Surface Area (TPSA): 262.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.92
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4790	47.90%
Caco-2	-	0.8880	88.80%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8714	87.14%
Subcellular localzation	Mitochondria	0.8017	80.17%
OATP2B1 inhibitior	-	0.8641	86.41%
OATP1B1 inhibitior	+	0.8551	85.51%
OATP1B3 inhibitior	+	0.9446	94.46%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9412	94.12%
P-glycoprotein inhibitior	+	0.6814	68.14%
P-glycoprotein substrate	+	0.7242	72.42%
CYP3A4 substrate	+	0.7290	72.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8663	86.63%
CYP3A4 inhibition	-	0.8764	87.64%
CYP2C9 inhibition	-	0.8703	87.03%
CYP2C19 inhibition	-	0.8525	85.25%
CYP2D6 inhibition	-	0.9028	90.28%
CYP1A2 inhibition	-	0.8697	86.97%
CYP2C8 inhibition	+	0.8478	84.78%
CYP inhibitory promiscuity	-	0.8566	85.66%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6095	60.95%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.8028	80.28%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8207	82.07%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7413	74.13%
skin sensitisation	-	0.8564	85.64%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9371	93.71%
Acute Oral Toxicity (c)	III	0.4878	48.78%
Estrogen receptor binding	+	0.8096	80.96%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5428	54.28%
Glucocorticoid receptor binding	+	0.7018	70.18%
Aromatase binding	+	0.5301	53.01%
PPAR gamma	+	0.7501	75.01%
Honey bee toxicity	-	0.6595	65.95%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9054	90.54%

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	99.57%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.96%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.59%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.19%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.11%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.19%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	95.14%	86.92%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.16%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	92.89%	91.49%
CHEMBL4302	P08183	P-glycoprotein 1	92.71%	92.98%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	91.97%	97.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.85%	92.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.55%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.51%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	90.47%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.84%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.78%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.88%	95.89%
CHEMBL3194	P02766	Transthyretin	86.98%	90.71%
CHEMBL4208	P20618	Proteasome component C5	86.10%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.05%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	84.85%	91.19%
CHEMBL2581	P07339	Cathepsin D	84.70%	98.95%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	84.33%	97.31%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.28%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.99%	94.00%
CHEMBL4581	P52732	Kinesin-like protein 1	81.87%	93.18%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.77%	96.90%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.35%	95.17%

Plants that contains it

• Buddleja davidii
• Marrubium alysson
• Phlomis bourgaei
• Phlomis herba-venti subsp. pungens
• Phlomis kotschyana
• Schnabelia tetradonta
• Stachys officinalis
• Verbascum thapsus
• Verbascum wiedemannianum

Cross-Links

• PubChem: 131885703
• LOTUS: LTS0268100
• wikiData: Q104398978