Benzyl ferulate

Details

• Internal ID: c04afd38-2d5d-4616-b88b-46824a225767
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: benzyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC2=CC=CC=C2)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OCC2=CC=CC=C2)O
• InChI: InChI=1S/C17H16O4/c1-20-16-11-13(7-9-15(16)18)8-10-17(19)21-12-14-5-3-2-4-6-14/h2-11,18H,12H2,1H3/b10-8+
• InChI Key: DZAPHTCUSDTZAT-CSKARUKUSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₄
• Molecular Weight: 284.31 g/mol
• Exact Mass: 284.10485899 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.16
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• Benzyl (E)-Ferulate
• 132335-97-8
• benzyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• (E)-Benzyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
• CHEMBL457076
• MEGxp0_000780
• SCHEMBL16155887
• ACon1_000937
• DZAPHTCUSDTZAT-CSKARUKUSA-N
• BDBM50131683
• AKOS000863238
• NCGC00169212-01
• (E)-3-(4-Hydroxy-3-methoxyphenyl)propenoic acid benzyl ester
• 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, phenylmethyl ester, (2E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9909	99.09%
Caco-2	+	0.5496	54.96%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.9075	90.75%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9254	92.54%
OATP1B3 inhibitior	+	0.9677	96.77%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8463	84.63%
P-glycoprotein inhibitior	-	0.8974	89.74%
P-glycoprotein substrate	-	0.9441	94.41%
CYP3A4 substrate	-	0.5250	52.50%
CYP2C9 substrate	-	0.6043	60.43%
CYP2D6 substrate	-	0.8380	83.80%
CYP3A4 inhibition	-	0.7629	76.29%
CYP2C9 inhibition	+	0.6576	65.76%
CYP2C19 inhibition	-	0.5785	57.85%
CYP2D6 inhibition	-	0.9179	91.79%
CYP1A2 inhibition	-	0.5273	52.73%
CYP2C8 inhibition	+	0.8492	84.92%
CYP inhibitory promiscuity	+	0.6244	62.44%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7487	74.87%
Carcinogenicity (trinary)	Non-required	0.6862	68.62%
Eye corrosion	-	0.9807	98.07%
Eye irritation	+	0.7473	74.73%
Skin irritation	-	0.7012	70.12%
Skin corrosion	-	0.9832	98.32%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3595	35.95%
Micronuclear	+	0.5673	56.73%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8467	84.67%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.8875	88.75%
Nephrotoxicity	-	0.8545	85.45%
Acute Oral Toxicity (c)	III	0.7202	72.02%
Estrogen receptor binding	+	0.9287	92.87%
Androgen receptor binding	+	0.8699	86.99%
Thyroid receptor binding	-	0.5608	56.08%
Glucocorticoid receptor binding	+	0.6090	60.90%
Aromatase binding	+	0.6768	67.68%
PPAR gamma	+	0.6546	65.46%
Honey bee toxicity	-	0.9020	90.20%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5245	52.45%
Fish aquatic toxicity	+	0.9884	98.84%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3729	P22748	Carbonic anhydrase IV	39500 nM	Ki	PMID: 26498394
CHEMBL3594	Q16790	Carbonic anhydrase IX	1030 nM	Ki	PMID: 26498394
CHEMBL4789	P35218	Carbonic anhydrase VA	880 nM; 880 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL3969	Q9Y2D0	Carbonic anhydrase VB	660 nM; 660 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL3025	P23280	Carbonic anhydrase VI	420 nM; 420 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	630 nM; 630 nM	Ki; Ki	PMID: 26498394; via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	8890 nM	Ki	PMID: 26498394
CHEMBL3510	Q9ULX7	Carbonic anhydrase XIV	780 nM; 780 nM	Ki; Ki	PMID: 26498394; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.17%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.29%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.83%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.74%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.37%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.96%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	92.29%	95.50%
CHEMBL2581	P07339	Cathepsin D	89.92%	98.95%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.66%	91.71%
CHEMBL3194	P02766	Transthyretin	85.46%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	83.87%	91.49%
CHEMBL2535	P11166	Glucose transporter	83.22%	98.75%
CHEMBL4208	P20618	Proteasome component C5	81.79%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.98%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	80.87%	94.73%

Plants that contains it

• Anodendron affine
• Cedrela salvadorensis
• Galium latoramosum
• Garcinia gummi-gutta
• Hertia cheirifolia
• Licaria chrysophylla
• Ormosia hosiei
• Ornithoglossum viride
• Petasites japonicus
• Petasites radiatus
• Populus euphratica
• Populus grandidentata
• Schizanthus tricolor
• Sphaeranthus confertifolius

Cross-Links

• PubChem: 7766335
• NPASS: NPC289459
• ChEMBL: CHEMBL457076
• LOTUS: LTS0220204
• wikiData: Q105347311