2,3-dimethoxy-4-[(E)-3-phenylprop-2-enyl]phenol

Details

• Internal ID: 046ada97-fca1-4fce-8cc9-4c845d05bbd0
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: 2,3-dimethoxy-4-[(E)-3-phenylprop-2-enyl]phenol
• SMILES (Canonical): COC1=C(C=CC(=C1OC)O)CC=CC2=CC=CC=C2
• SMILES (Isomeric): COC1=C(C=CC(=C1OC)O)C/C=C/C2=CC=CC=C2
• InChI: InChI=1S/C17H18O3/c1-19-16-14(11-12-15(18)17(16)20-2)10-6-9-13-7-4-3-5-8-13/h3-9,11-12,18H,10H2,1-2H3/b9-6+
• InChI Key: ANZREKWPXVZUPG-RMKNXTFCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.32 g/mol
• Exact Mass: 270.125594432 g/mol
• Topological Polar Surface Area (TPSA): 38.70 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.67
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.8527	85.27%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8079	80.79%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.7828	78.28%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6528	65.28%
P-glycoprotein inhibitior	-	0.8072	80.72%
P-glycoprotein substrate	-	0.9505	95.05%
CYP3A4 substrate	-	0.6384	63.84%
CYP2C9 substrate	+	0.5888	58.88%
CYP2D6 substrate	+	0.4021	40.21%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8502	85.02%
CYP2C19 inhibition	+	0.8234	82.34%
CYP2D6 inhibition	-	0.8172	81.72%
CYP1A2 inhibition	+	0.7594	75.94%
CYP2C8 inhibition	+	0.5296	52.96%
CYP inhibitory promiscuity	+	0.8570	85.70%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.7621	76.21%
Carcinogenicity (trinary)	Non-required	0.5798	57.98%
Eye corrosion	-	0.9482	94.82%
Eye irritation	+	0.6984	69.84%
Skin irritation	-	0.6568	65.68%
Skin corrosion	-	0.9257	92.57%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7526	75.26%
Micronuclear	-	0.5108	51.08%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	+	0.5314	53.14%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	-	0.7477	74.77%
Acute Oral Toxicity (c)	III	0.7794	77.94%
Estrogen receptor binding	+	0.8924	89.24%
Androgen receptor binding	+	0.6179	61.79%
Thyroid receptor binding	+	0.5328	53.28%
Glucocorticoid receptor binding	+	0.5419	54.19%
Aromatase binding	+	0.6413	64.13%
PPAR gamma	+	0.5609	56.09%
Honey bee toxicity	-	0.9236	92.36%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9723	97.23%

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	98.67%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.44%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.87%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.81%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.15%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.44%	96.09%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	89.30%	91.71%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	88.98%	94.62%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.56%	94.08%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.01%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.62%	99.15%
CHEMBL2581	P07339	Cathepsin D	83.33%	98.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.52%	90.24%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.14%	95.50%

Plants that contains it

• Machaerium mucronulatum

Cross-Links

• PubChem: 12312982
• LOTUS: LTS0240163
• wikiData: Q76422769