3-(2,6-Dihydroxy-4-methoxyphenyl)-1-phenylpropan-1-one

Details

• Internal ID: 8849c5ba-a7d7-46f9-bbda-77389ae07f53
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retro-dihydrochalcones
• IUPAC Name: 3-(2,6-dihydroxy-4-methoxyphenyl)-1-phenylpropan-1-one
• SMILES (Canonical): COC1=CC(=C(C(=C1)O)CCC(=O)C2=CC=CC=C2)O
• SMILES (Isomeric): COC1=CC(=C(C(=C1)O)CCC(=O)C2=CC=CC=C2)O
• InChI: InChI=1S/C16H16O4/c1-20-12-9-15(18)13(16(19)10-12)7-8-14(17)11-5-3-2-4-6-11/h2-6,9-10,18-19H,7-8H2,1H3
• InChI Key: YKQDHGLAIZBHEU-UHFFFAOYSA-N
• Popularity: 3 references 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: 2.80
• Atomic LogP (AlogP): 2.92
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9356	93.56%
Caco-2	+	0.7454	74.54%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.9161	91.61%
OATP2B1 inhibitior	-	0.5826	58.26%
OATP1B1 inhibitior	+	0.8844	88.44%
OATP1B3 inhibitior	+	0.9516	95.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5502	55.02%
P-glycoprotein inhibitior	-	0.7633	76.33%
P-glycoprotein substrate	-	0.9433	94.33%
CYP3A4 substrate	-	0.6220	62.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3530	35.30%
CYP3A4 inhibition	+	0.5801	58.01%
CYP2C9 inhibition	+	0.7841	78.41%
CYP2C19 inhibition	+	0.9222	92.22%
CYP2D6 inhibition	-	0.7543	75.43%
CYP1A2 inhibition	+	0.9486	94.86%
CYP2C8 inhibition	+	0.6999	69.99%
CYP inhibitory promiscuity	+	0.7068	70.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8234	82.34%
Carcinogenicity (trinary)	Non-required	0.7148	71.48%
Eye corrosion	-	0.9794	97.94%
Eye irritation	+	0.9046	90.46%
Skin irritation	-	0.6979	69.79%
Skin corrosion	-	0.8706	87.06%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6060	60.60%
Micronuclear	-	0.5882	58.82%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6801	68.01%
Acute Oral Toxicity (c)	III	0.7181	71.81%
Estrogen receptor binding	+	0.7804	78.04%
Androgen receptor binding	+	0.6393	63.93%
Thyroid receptor binding	-	0.5890	58.90%
Glucocorticoid receptor binding	-	0.4787	47.87%
Aromatase binding	+	0.5643	56.43%
PPAR gamma	+	0.6211	62.11%
Honey bee toxicity	-	0.9543	95.43%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6555	65.55%
Fish aquatic toxicity	+	0.8770	87.70%

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	94.75%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.24%	86.33%
CHEMBL240	Q12809	HERG	94.04%	89.76%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.45%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.20%	95.56%
CHEMBL2535	P11166	Glucose transporter	91.97%	98.75%
CHEMBL2581	P07339	Cathepsin D	89.21%	98.95%
CHEMBL4208	P20618	Proteasome component C5	88.29%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.27%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.11%	99.15%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.56%	95.50%
CHEMBL3401	O75469	Pregnane X receptor	80.40%	94.73%

Plants that contains it

• Mitrella kentii
• Piper aduncum
• Populus laurifolia

Cross-Links

• PubChem: 162966195
• LOTUS: LTS0208379
• wikiData: Q105349845