1-(2-Methoxy-4-hydroxyphenyl)-3-(4-hydroxy-phenyl)propan-2-one

Details

• Internal ID: 28c953b7-62a1-4c99-8a9b-21a197306185
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: 1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)propan-2-one
• SMILES (Canonical): COC1=C(C=CC(=C1)O)CC(=O)CC2=CC=C(C=C2)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)O)CC(=O)CC2=CC=C(C=C2)O
• InChI: InChI=1S/C16H16O4/c1-20-16-10-14(18)7-4-12(16)9-15(19)8-11-2-5-13(17)6-3-11/h2-7,10,17-18H,8-9H2,1H3
• InChI Key: MFOUUOIYBNKWEE-UHFFFAOYSA-N
• Popularity: 1 reference 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: 2.40
• Atomic LogP (AlogP): 2.46
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• 1-(2-methoxy-4-hydroxyphenyl)-3-(4-hydroxy-phenyl)propan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	+	0.9254	92.54%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.9301	93.01%
OATP2B1 inhibitior	-	0.8526	85.26%
OATP1B1 inhibitior	+	0.9078	90.78%
OATP1B3 inhibitior	+	0.9508	95.08%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5303	53.03%
P-glycoprotein inhibitior	-	0.7526	75.26%
P-glycoprotein substrate	-	0.7843	78.43%
CYP3A4 substrate	-	0.5243	52.43%
CYP2C9 substrate	-	0.7970	79.70%
CYP2D6 substrate	+	0.4083	40.83%
CYP3A4 inhibition	-	0.7152	71.52%
CYP2C9 inhibition	+	0.5524	55.24%
CYP2C19 inhibition	+	0.9255	92.55%
CYP2D6 inhibition	-	0.8178	81.78%
CYP1A2 inhibition	+	0.8797	87.97%
CYP2C8 inhibition	+	0.7395	73.95%
CYP inhibitory promiscuity	+	0.7286	72.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7088	70.88%
Carcinogenicity (trinary)	Non-required	0.6475	64.75%
Eye corrosion	-	0.9694	96.94%
Eye irritation	+	0.9576	95.76%
Skin irritation	-	0.7364	73.64%
Skin corrosion	-	0.9697	96.97%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4458	44.58%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.6091	60.91%
skin sensitisation	-	0.8919	89.19%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.6875	68.75%
Nephrotoxicity	-	0.5868	58.68%
Acute Oral Toxicity (c)	III	0.6193	61.93%
Estrogen receptor binding	+	0.9175	91.75%
Androgen receptor binding	-	0.5159	51.59%
Thyroid receptor binding	+	0.6283	62.83%
Glucocorticoid receptor binding	+	0.6781	67.81%
Aromatase binding	+	0.6679	66.79%
PPAR gamma	+	0.6171	61.71%
Honey bee toxicity	-	0.8882	88.82%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6104	61.04%
Fish aquatic toxicity	+	0.9354	93.54%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.16%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.22%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.10%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.32%	98.95%
CHEMBL2535	P11166	Glucose transporter	91.37%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	91.12%	90.20%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.40%	96.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.62%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.23%	95.89%
CHEMBL4208	P20618	Proteasome component C5	87.16%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.02%	95.56%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	85.15%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.43%	95.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.49%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.46%	85.14%

Plants that contains it

• Xanthocercis zambesiaca

Cross-Links

• PubChem: 14160604
• LOTUS: LTS0187459
• wikiData: Q105162902