(E)-4-(4-hydroxy-3-methoxyphenyl)-3-methylbut-3-en-2-one

Details

• Internal ID: 38943410-a09a-4930-8b2f-0af5d1e183cc
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives
• IUPAC Name: (E)-4-(4-hydroxy-3-methoxyphenyl)-3-methylbut-3-en-2-one
• SMILES (Canonical): CC(=CC1=CC(=C(C=C1)O)OC)C(=O)C
• SMILES (Isomeric): C/C(=C\C1=CC(=C(C=C1)O)OC)/C(=O)C
• InChI: InChI=1S/C12H14O3/c1-8(9(2)13)6-10-4-5-11(14)12(7-10)15-3/h4-7,14H,1-3H3/b8-6+
• InChI Key: KCKUAOCDLPUJHW-SOFGYWHQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄O₃
• Molecular Weight: 206.24 g/mol
• Exact Mass: 206.094294304 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	+	0.8226	82.26%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8419	84.19%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9561	95.61%
OATP1B3 inhibitior	+	0.9703	97.03%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.7227	72.27%
P-glycoprotein inhibitior	-	0.9717	97.17%
P-glycoprotein substrate	-	0.9705	97.05%
CYP3A4 substrate	-	0.6259	62.59%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.7868	78.68%
CYP3A4 inhibition	-	0.7106	71.06%
CYP2C9 inhibition	-	0.9234	92.34%
CYP2C19 inhibition	+	0.5336	53.36%
CYP2D6 inhibition	-	0.9155	91.55%
CYP1A2 inhibition	-	0.5095	50.95%
CYP2C8 inhibition	-	0.6578	65.78%
CYP inhibitory promiscuity	+	0.5154	51.54%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7553	75.53%
Carcinogenicity (trinary)	Non-required	0.6240	62.40%
Eye corrosion	-	0.6484	64.84%
Eye irritation	+	0.9487	94.87%
Skin irritation	+	0.6742	67.42%
Skin corrosion	-	0.9682	96.82%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5981	59.81%
Micronuclear	-	0.5167	51.67%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.6296	62.96%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	-	0.8750	87.50%
Nephrotoxicity	-	0.7286	72.86%
Acute Oral Toxicity (c)	III	0.7982	79.82%
Estrogen receptor binding	+	0.6891	68.91%
Androgen receptor binding	-	0.5864	58.64%
Thyroid receptor binding	-	0.6854	68.54%
Glucocorticoid receptor binding	-	0.7452	74.52%
Aromatase binding	-	0.6093	60.93%
PPAR gamma	-	0.5408	54.08%
Honey bee toxicity	-	0.9335	93.35%
Biodegradation	+	0.5250	52.50%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9482	94.82%

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	98.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.48%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.62%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.21%	86.33%
CHEMBL3194	P02766	Transthyretin	87.95%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.91%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.76%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.76%	96.00%
CHEMBL2535	P11166	Glucose transporter	85.03%	98.75%
CHEMBL4208	P20618	Proteasome component C5	84.52%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.06%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.71%	89.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.55%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	80.22%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.01%	95.50%

Plants that contains it

• Machilus wangchiana

Cross-Links

• PubChem: 68254945
• LOTUS: LTS0025840
• wikiData: Q105138806