2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, 2-(4-hydroxyphenyl)ethyl ester, (E)-; 4-Hydroxyphenethyl trans-ferulate

Details

• Internal ID: 096b6aa6-8936-4a9e-b179-46b51c549756
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 2-(4-hydroxyphenyl)ethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCCC2=CC=C(C=C2)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C=CC(=O)OCCC2=CC=C(C=C2)O)O
• InChI: InChI=1S/C18H18O5/c1-22-17-12-14(4-8-16(17)20)5-9-18(21)23-11-10-13-2-6-15(19)7-3-13/h2-9,12,19-20H,10-11H2,1H3
• InChI Key: JMSFLLZUCIXALN-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₅
• Molecular Weight: 314.30 g/mol
• Exact Mass: 314.11542367 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9780	97.80%
Caco-2	+	0.5720	57.20%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.9192	91.92%
OATP2B1 inhibitior	-	0.8536	85.36%
OATP1B1 inhibitior	+	0.9204	92.04%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	0.5600	56.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9538	95.38%
P-glycoprotein inhibitior	-	0.7556	75.56%
P-glycoprotein substrate	-	0.8183	81.83%
CYP3A4 substrate	+	0.5290	52.90%
CYP2C9 substrate	-	0.7914	79.14%
CYP2D6 substrate	-	0.8167	81.67%
CYP3A4 inhibition	-	0.7704	77.04%
CYP2C9 inhibition	+	0.8113	81.13%
CYP2C19 inhibition	+	0.8019	80.19%
CYP2D6 inhibition	-	0.8723	87.23%
CYP1A2 inhibition	+	0.8225	82.25%
CYP2C8 inhibition	+	0.9192	91.92%
CYP inhibitory promiscuity	+	0.5342	53.42%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8071	80.71%
Carcinogenicity (trinary)	Non-required	0.7150	71.50%
Eye corrosion	-	0.9878	98.78%
Eye irritation	+	0.5935	59.35%
Skin irritation	-	0.8358	83.58%
Skin corrosion	-	0.9773	97.73%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3744	37.44%
Micronuclear	-	0.6490	64.90%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.8642	86.42%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.8815	88.15%
Acute Oral Toxicity (c)	III	0.7550	75.50%
Estrogen receptor binding	+	0.9364	93.64%
Androgen receptor binding	+	0.9027	90.27%
Thyroid receptor binding	+	0.5330	53.30%
Glucocorticoid receptor binding	+	0.7800	78.00%
Aromatase binding	+	0.7925	79.25%
PPAR gamma	+	0.6036	60.36%
Honey bee toxicity	-	0.8495	84.95%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9595	95.95%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3594	Q16790	Carbonic anhydrase IX	810 nM	Ki	via Super-PRED
CHEMBL4789	P35218	Carbonic anhydrase VA	810 nM	Ki	via Super-PRED
CHEMBL3969	Q9Y2D0	Carbonic anhydrase VB	670 nM	Ki	via Super-PRED
CHEMBL3025	P23280	Carbonic anhydrase VI	770 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	620 nM	Ki	via Super-PRED
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	720 nM	Ki	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.80%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.73%	91.11%
CHEMBL3194	P02766	Transthyretin	95.72%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.20%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.81%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.86%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.32%	95.56%
CHEMBL2535	P11166	Glucose transporter	87.25%	98.75%
CHEMBL4208	P20618	Proteasome component C5	86.33%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.88%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.65%	96.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.10%	91.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.35%	89.00%

Plants that contains it

• Angelica sinensis
• Chaerophyllum hirsutum
• Coriandrum sativum
• Glehnia littoralis
• Hansenia forbesii
• Heracleum maximum
• Oenanthe javanica
• Sida spinosa

Cross-Links

• PubChem: 20979927
• LOTUS: LTS0196798
• wikiData: Q105131627