2,4-Dihydroxy-6-phenethyl-benzoic acid methyl ester

Details

• Internal ID: 1e6f8fb6-3ae9-454e-9feb-6c43fc94c600
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: methyl 2,4-dihydroxy-6-(2-phenylethyl)benzoate
• SMILES (Canonical): COC(=O)C1=C(C=C(C=C1O)O)CCC2=CC=CC=C2
• SMILES (Isomeric): COC(=O)C1=C(C=C(C=C1O)O)CCC2=CC=CC=C2
• InChI: InChI=1S/C16H16O4/c1-20-16(19)15-12(9-13(17)10-14(15)18)8-7-11-5-3-2-4-6-11/h2-6,9-10,17-18H,7-8H2,1H3
• InChI Key: ROMUMXDSMIIOLM-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₄
• Molecular Weight: 272.29 g/mol
• Exact Mass: 272.10485899 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8874	88.74%
Caco-2	+	0.8417	84.17%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.9136	91.36%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.9399	93.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6719	67.19%
P-glycoprotein inhibitior	-	0.7849	78.49%
P-glycoprotein substrate	-	0.7613	76.13%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6146	61.46%
CYP2D6 substrate	-	0.8347	83.47%
CYP3A4 inhibition	-	0.5837	58.37%
CYP2C9 inhibition	+	0.8887	88.87%
CYP2C19 inhibition	+	0.8420	84.20%
CYP2D6 inhibition	-	0.8720	87.20%
CYP1A2 inhibition	+	0.8121	81.21%
CYP2C8 inhibition	+	0.8613	86.13%
CYP inhibitory promiscuity	+	0.7091	70.91%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7645	76.45%
Carcinogenicity (trinary)	Non-required	0.7324	73.24%
Eye corrosion	-	0.9801	98.01%
Eye irritation	+	0.7771	77.71%
Skin irritation	-	0.6623	66.23%
Skin corrosion	-	0.8948	89.48%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4549	45.49%
Micronuclear	-	0.5441	54.41%
Hepatotoxicity	+	0.5552	55.52%
skin sensitisation	-	0.9255	92.55%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.5667	56.67%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.4688	46.88%
Acute Oral Toxicity (c)	III	0.6039	60.39%
Estrogen receptor binding	+	0.8665	86.65%
Androgen receptor binding	+	0.7199	71.99%
Thyroid receptor binding	-	0.5339	53.39%
Glucocorticoid receptor binding	+	0.5733	57.33%
Aromatase binding	+	0.6767	67.67%
PPAR gamma	+	0.6648	66.48%
Honey bee toxicity	-	0.8745	87.45%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9598	95.98%

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	97.31%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.99%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.98%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.09%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.90%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	90.62%	94.73%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	90.08%	95.17%
CHEMBL2535	P11166	Glucose transporter	88.90%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.52%	95.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.80%	96.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.91%	95.56%
CHEMBL4208	P20618	Proteasome component C5	81.60%	90.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	80.33%	92.67%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	80.20%	94.62%

Plants that contains it

• Boesenbergia rotunda

Cross-Links

• PubChem: 14195786
• LOTUS: LTS0110306
• wikiData: Q105242327