4-Methoxychalcone

Details

• Internal ID: 5625cf24-ca9f-46b8-984a-d4c75837e0ac
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retrochalcones
• IUPAC Name: (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
• SMILES (Canonical): COC1=CC=C(C=C1)C=CC(=O)C2=CC=CC=C2
• SMILES (Isomeric): COC1=CC=C(C=C1)/C=C/C(=O)C2=CC=CC=C2
• InChI: InChI=1S/C16H14O2/c1-18-15-10-7-13(8-11-15)9-12-16(17)14-5-3-2-4-6-14/h2-12H,1H3/b12-9+
• InChI Key: XUFXKBJMCRJATM-FMIVXFBMSA-N
• Popularity: 135 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28 g/mol
• Exact Mass: 238.099379685 g/mol
• Topological Polar Surface Area (TPSA): 26.30 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.59
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 959-33-1
• (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
• 22252-15-9
• (2E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
• Chalcone, 4-methoxy-
• 3-(4-Methoxyphenyl)-1-phenyl-2-propen-1-one
• 2-Propen-1-one, 3-(4-methoxyphenyl)-1-phenyl-
• 2-(4-Methoxybenzal)acetophenone
• 4'-Methoxybenzylideneacetophenone
• 2-propen-1-one, 3-(4-methoxyphenyl)-1-phenyl-, (2E)-
• MFCD00017179
• (E)-3-(4-methoxyphenyl)-1-phenyl-prop-2-en-1-one
• Phenyl p-methoxystyryl ketone
• 3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one
• 2-(4-Methoxybenzylidene)acetophenone
• NSC636917
• p-Methoxyphenyl styryl ketone
• NSC 11866
• Chalcone, 4
• 3-(4-Methoxy-phenyl)-1-phenyl-propenone
• trans-4-Methoxychalcone
• 2-(p-Anisal)acetophenone
• p-Methoxystyryl phenyl ketone
• 4-Methoxystyryl phenyl ketone
• 2-(p-Anisylidene)acetophenone
• SCHEMBL521906
• (2E)-3-(4-Methoxyphenyl)-1-phenyl-2-propen-1-one
• CHEMBL105496
• SCHEMBL1566431
• BDBM86005
• (p-Methoxybenzylidene)acetophenone
• (4-Methoxybenzylidene)acetophenone
• DTXSID601313945
• NSC11866
• XAA25215
• NSC-11866
• NSC170287
• AKOS000447894
• NSC-170287
• NSC-636917
• LS-14472
• BB 0221143
• CS-0181937
• M1409
• EN300-16058
• 1-Phenyl-3-(4-methoxyphenyl)-2-propen-1-one
• A23188
• S10243
• 1-Phenyl-3-(4-methoxyphenyl)-2-propen- 1-one
• 2-Propen-1-one,3-(4-methoxyphenyl)-1-phenyl-
• 10L-722
• A878641
• AE-641/00576037
• W-100150
• Q63395979
• Z46028374
• InChI=1/C16H14O2/c1-18-15-10-7-13(8-11-15)9-12-16(17)14-5-3-2-4-6-14/h2-12H,1H3/b12-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.9314	93.14%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8272	82.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9629	96.29%
OATP1B3 inhibitior	+	0.9761	97.61%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6480	64.80%
P-glycoprotein inhibitior	-	0.8498	84.98%
P-glycoprotein substrate	-	0.9798	97.98%
CYP3A4 substrate	-	0.6332	63.32%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.7807	78.07%
CYP3A4 inhibition	-	0.8105	81.05%
CYP2C9 inhibition	-	0.5941	59.41%
CYP2C19 inhibition	+	0.8926	89.26%
CYP2D6 inhibition	-	0.9466	94.66%
CYP1A2 inhibition	+	0.9573	95.73%
CYP2C8 inhibition	+	0.5924	59.24%
CYP inhibitory promiscuity	+	0.7458	74.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5959	59.59%
Carcinogenicity (trinary)	Non-required	0.4414	44.14%
Eye corrosion	-	0.8336	83.36%
Eye irritation	+	0.9821	98.21%
Skin irritation	-	0.6957	69.57%
Skin corrosion	-	0.9922	99.22%
Ames mutagenesis	-	1.0000	100.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3833	38.33%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5894	58.94%
skin sensitisation	+	0.7031	70.31%
Respiratory toxicity	-	0.8778	87.78%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	-	0.9000	90.00%
Nephrotoxicity	-	0.5952	59.52%
Acute Oral Toxicity (c)	III	0.8488	84.88%
Estrogen receptor binding	+	0.8877	88.77%
Androgen receptor binding	+	0.8023	80.23%
Thyroid receptor binding	-	0.6498	64.98%
Glucocorticoid receptor binding	-	0.5583	55.83%
Aromatase binding	+	0.7946	79.46%
PPAR gamma	-	0.5448	54.48%
Honey bee toxicity	-	0.9610	96.10%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9575	95.75%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.48%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.39%	86.33%
CHEMBL221	P23219	Cyclooxygenase-1	94.98%	90.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.48%	95.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.33%	96.00%
CHEMBL4208	P20618	Proteasome component C5	90.80%	90.00%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	89.56%	87.67%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.24%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.86%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.63%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.69%	96.09%
CHEMBL2535	P11166	Glucose transporter	83.91%	98.75%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.19%	94.08%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.49%	81.11%

Plants that contains it

• Ficus lyrata

Cross-Links

• PubChem: 641819
• LOTUS: LTS0215632
• wikiData: Q63395979