3-[4-Methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid

Details

• Internal ID: 227d0714-1f12-4bd1-9262-66f8cac10fa7
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Cinnamic acids
• IUPAC Name: 3-[4-methoxy-3-(3-methylbut-2-enyl)phenyl]prop-2-enoic acid
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1)C=CC(=O)O)OC)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1)C=CC(=O)O)OC)C
• InChI: InChI=1S/C15H18O3/c1-11(2)4-7-13-10-12(6-9-15(16)17)5-8-14(13)18-3/h4-6,8-10H,7H2,1-3H3,(H,16,17)
• InChI Key: XWVOBHSSIJXKCV-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.30 g/mol
• Exact Mass: 246.125594432 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.30
• H-Bond Acceptor: 2
• 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	+	0.9973	99.73%
Caco-2	+	0.9145	91.45%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8768	87.68%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9297	92.97%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5484	54.84%
P-glycoprotein inhibitior	-	0.9728	97.28%
P-glycoprotein substrate	-	0.8688	86.88%
CYP3A4 substrate	-	0.5847	58.47%
CYP2C9 substrate	-	0.7907	79.07%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.8628	86.28%
CYP2C9 inhibition	-	0.7154	71.54%
CYP2C19 inhibition	-	0.5828	58.28%
CYP2D6 inhibition	-	0.8714	87.14%
CYP1A2 inhibition	-	0.7009	70.09%
CYP2C8 inhibition	+	0.4878	48.78%
CYP inhibitory promiscuity	+	0.5319	53.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.6419	64.19%
Carcinogenicity (trinary)	Non-required	0.6901	69.01%
Eye corrosion	-	0.9564	95.64%
Eye irritation	+	0.8103	81.03%
Skin irritation	-	0.5458	54.58%
Skin corrosion	-	0.9759	97.59%
Ames mutagenesis	-	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4529	45.29%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.6541	65.41%
skin sensitisation	-	0.6150	61.50%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	-	0.6961	69.61%
Acute Oral Toxicity (c)	III	0.8465	84.65%
Estrogen receptor binding	+	0.5981	59.81%
Androgen receptor binding	+	0.6408	64.08%
Thyroid receptor binding	-	0.6645	66.45%
Glucocorticoid receptor binding	-	0.5974	59.74%
Aromatase binding	+	0.7109	71.09%
PPAR gamma	+	0.7283	72.83%
Honey bee toxicity	-	0.9268	92.68%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7507	75.07%
Fish aquatic toxicity	+	0.9929	99.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.67%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.00%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.54%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.53%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.30%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.47%	85.14%
CHEMBL1255126	O15151	Protein Mdm4	87.25%	90.20%
CHEMBL221	P23219	Cyclooxygenase-1	86.95%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.66%	95.56%
CHEMBL2581	P07339	Cathepsin D	85.48%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.05%	95.50%
CHEMBL4208	P20618	Proteasome component C5	83.30%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.82%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.42%	94.45%
CHEMBL2535	P11166	Glucose transporter	80.19%	98.75%
CHEMBL3194	P02766	Transthyretin	80.05%	90.71%

Plants that contains it

• Baccharis neglecta

Cross-Links

• PubChem: 73185676
• LOTUS: LTS0126310
• wikiData: Q105343802