(Z)-3-(3,4-Dihydroxyphenyl)propenoic acid 2-phenylethyl ester

Details

• Internal ID: 0078c915-8989-4620-b83d-6868c44c9d27
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: 2-phenylethyl (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• SMILES (Canonical): C1=CC=C(C=C1)CCOC(=O)C=CC2=CC(=C(C=C2)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)CCOC(=O)/C=C\C2=CC(=C(C=C2)O)O
• InChI: InChI=1S/C17H16O4/c18-15-8-6-14(12-16(15)19)7-9-17(20)21-11-10-13-4-2-1-3-5-13/h1-9,12,18-19H,10-11H2/b9-7-
• InChI Key: SWUARLUWKZWEBQ-CLFYSBASSA-N
• Popularity: 0 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): 66.80 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 2.90
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• (Z)-3-(3,4-Dihydroxyphenyl)propenoic acid 2-phenylethyl ester
• 2-phenylethyl (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• Lopac-C-8221
• phenethyl (Z)-3-(3,4-dihydroxyphenyl)prop-2-enoate
• CHEMBL1397711
• AKOS025401276
• NCGC00015274-01

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9551	95.51%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.9106	91.06%
OATP2B1 inhibitior	-	0.8603	86.03%
OATP1B1 inhibitior	+	0.9419	94.19%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	+	0.8200	82.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6955	69.55%
P-glycoprotein inhibitior	-	0.9257	92.57%
P-glycoprotein substrate	-	0.9509	95.09%
CYP3A4 substrate	-	0.5560	55.60%
CYP2C9 substrate	-	0.5898	58.98%
CYP2D6 substrate	-	0.8417	84.17%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	+	0.5955	59.55%
CYP2C19 inhibition	+	0.8042	80.42%
CYP2D6 inhibition	-	0.8592	85.92%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	+	0.7825	78.25%
CYP inhibitory promiscuity	-	0.6362	63.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8341	83.41%
Carcinogenicity (trinary)	Non-required	0.6651	66.51%
Eye corrosion	-	0.9912	99.12%
Eye irritation	+	0.9133	91.33%
Skin irritation	-	0.8112	81.12%
Skin corrosion	-	0.9742	97.42%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4889	48.89%
Micronuclear	-	0.6008	60.08%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	+	0.4757	47.57%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	-	0.5111	51.11%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8852	88.52%
Acute Oral Toxicity (c)	III	0.7989	79.89%
Estrogen receptor binding	+	0.9485	94.85%
Androgen receptor binding	+	0.9588	95.88%
Thyroid receptor binding	-	0.5994	59.94%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.7899	78.99%
PPAR gamma	+	0.7256	72.56%
Honey bee toxicity	-	0.8406	84.06%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9828	98.28%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	46 nM	Ki	via Super-PRED
CHEMBL1900	P15121	Aldose reductase	570 nM	IC50	via Super-PRED
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	14125.4 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	794.3 nM; 794.3 nM; 130 nM	Potency; Potency; IC50	via Super-PRED; via CMAUP; via Super-PRED
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	970 nM	IC50	via Super-PRED
CHEMBL4096	P04637	Cellular tumor antigen p53	12589.3 nM; 31622.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL221	P23219	Cyclooxygenase-1	833 nM	IC50	via Super-PRED
CHEMBL3356	P05177	Cytochrome P450 1A2	1000 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	12589.25 nM	AC50	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	39810.7 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	39810.7 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	19952.6 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	25118.9 nM	Potency	via CMAUP
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	2238.7 nM; 2238.7 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	25118.9 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	656.1 nM	Potency	via Super-PRED
CHEMBL1293256	P40225	Thrombopoietin	251.2 nM; 251.2 nM; 251.2 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	5011.9 nM; 5011.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.30%	91.11%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	98.07%	94.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.63%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	93.44%	91.49%
CHEMBL2581	P07339	Cathepsin D	90.40%	98.95%
CHEMBL3194	P02766	Transthyretin	90.12%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.73%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.15%	99.17%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	88.67%	91.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.46%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.78%	96.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	86.46%	80.78%
CHEMBL5939	Q9NZ08	Endoplasmic reticulum aminopeptidase 1	82.18%	100.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.18%	95.50%

Plants that contains it

• Ephedra sinica
• Pleurolobus gangeticus
• Sida cordifolia

Cross-Links

• PubChem: 6603789
• NPASS: NPC141791
• ChEMBL: CHEMBL1397711