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

Details

• Internal ID: b90294d2-5e11-4f94-be29-9a1219c22165
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retro-dihydrochalcones
• IUPAC Name: 3-(2,6-dihydroxy-4-methoxyphenyl)-1-(4-hydroxyphenyl)propan-1-one
• SMILES (Canonical): COC1=CC(=C(C(=C1)O)CCC(=O)C2=CC=C(C=C2)O)O
• SMILES (Isomeric): COC1=CC(=C(C(=C1)O)CCC(=O)C2=CC=C(C=C2)O)O
• InChI: InChI=1S/C16H16O5/c1-21-12-8-15(19)13(16(20)9-12)6-7-14(18)10-2-4-11(17)5-3-10/h2-5,8-9,17,19-20H,6-7H2,1H3
• InChI Key: DCCXVROJIFHCQK-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.29 g/mol
• Exact Mass: 288.09977361 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.63
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• 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	+	0.8687	86.87%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.9161	91.61%
OATP2B1 inhibitior	+	0.5525	55.25%
OATP1B1 inhibitior	+	0.8416	84.16%
OATP1B3 inhibitior	+	0.9516	95.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6108	61.08%
P-glycoprotein inhibitior	-	0.6947	69.47%
P-glycoprotein substrate	-	0.8925	89.25%
CYP3A4 substrate	-	0.5928	59.28%
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	+	0.7947	79.47%
CYP inhibitory promiscuity	+	0.7068	70.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8234	82.34%
Carcinogenicity (trinary)	Non-required	0.7148	71.48%
Eye corrosion	-	0.9794	97.94%
Eye irritation	+	0.9337	93.37%
Skin irritation	-	0.6979	69.79%
Skin corrosion	-	0.8706	87.06%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7487	74.87%
Micronuclear	-	0.5882	58.82%
Hepatotoxicity	-	0.7375	73.75%
skin sensitisation	-	0.8942	89.42%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.6484	64.84%
Acute Oral Toxicity (c)	III	0.7181	71.81%
Estrogen receptor binding	+	0.8677	86.77%
Androgen receptor binding	+	0.8614	86.14%
Thyroid receptor binding	+	0.6089	60.89%
Glucocorticoid receptor binding	+	0.7124	71.24%
Aromatase binding	+	0.7161	71.61%
PPAR gamma	+	0.7169	71.69%
Honey bee toxicity	-	0.9548	95.48%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
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	94.63%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.99%	99.17%
CHEMBL4208	P20618	Proteasome component C5	92.87%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.67%	86.33%
CHEMBL2535	P11166	Glucose transporter	89.54%	98.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.26%	96.09%
CHEMBL3192	Q9BY41	Histone deacetylase 8	87.44%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.48%	95.56%
CHEMBL2581	P07339	Cathepsin D	84.03%	98.95%
CHEMBL3194	P02766	Transthyretin	82.40%	90.71%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.72%	85.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.55%	91.07%

Plants that contains it

• Sorghum bicolor

Cross-Links

• PubChem: 162969495
• LOTUS: LTS0013003
• wikiData: Q104975206