2-Hydroxy-4,5,6-trimethoxydihydrochalcone

Details

• Internal ID: bb107992-92c0-44e8-a383-4c901dc7aad0
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Chalcones and dihydrochalcones > Retro-dihydrochalcones
• IUPAC Name: 3-(6-hydroxy-2,3,4-trimethoxyphenyl)-1-phenylpropan-1-one
• SMILES (Canonical): COC1=C(C(=C(C(=C1)O)CCC(=O)C2=CC=CC=C2)OC)OC
• SMILES (Isomeric): COC1=C(C(=C(C(=C1)O)CCC(=O)C2=CC=CC=C2)OC)OC
• InChI: InChI=1S/C18H20O5/c1-21-16-11-15(20)13(17(22-2)18(16)23-3)9-10-14(19)12-7-5-4-6-8-12/h4-8,11,20H,9-10H2,1-3H3
• InChI Key: XXHGGLKQZUXJDI-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.13107373 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• CHEBI:187176
• LMPK12120610
• 3-(6-hydroxy-2,3,4-trimethoxyphenyl)-1-phenylpropan-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9719	97.19%
Caco-2	+	0.8847	88.47%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.9155	91.55%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	+	0.9112	91.12%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.7147	71.47%
P-glycoprotein inhibitior	+	0.5762	57.62%
P-glycoprotein substrate	-	0.8568	85.68%
CYP3A4 substrate	-	0.5528	55.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3530	35.30%
CYP3A4 inhibition	-	0.7873	78.73%
CYP2C9 inhibition	-	0.7115	71.15%
CYP2C19 inhibition	+	0.8095	80.95%
CYP2D6 inhibition	-	0.8506	85.06%
CYP1A2 inhibition	+	0.7523	75.23%
CYP2C8 inhibition	+	0.8279	82.79%
CYP inhibitory promiscuity	-	0.5273	52.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7643	76.43%
Carcinogenicity (trinary)	Non-required	0.6616	66.16%
Eye corrosion	-	0.9800	98.00%
Eye irritation	-	0.5136	51.36%
Skin irritation	-	0.7695	76.95%
Skin corrosion	-	0.9549	95.49%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5405	54.05%
Micronuclear	-	0.7167	71.67%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9065	90.65%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8037	80.37%
Acute Oral Toxicity (c)	III	0.7605	76.05%
Estrogen receptor binding	+	0.8325	83.25%
Androgen receptor binding	-	0.5472	54.72%
Thyroid receptor binding	+	0.5924	59.24%
Glucocorticoid receptor binding	+	0.6661	66.61%
Aromatase binding	-	0.6697	66.97%
PPAR gamma	+	0.5850	58.50%
Honey bee toxicity	-	0.9494	94.94%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6504	65.04%
Fish aquatic toxicity	+	0.8933	89.33%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.12%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.93%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.22%	99.17%
CHEMBL2535	P11166	Glucose transporter	92.97%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	92.45%	90.20%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.13%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.38%	95.50%
CHEMBL4208	P20618	Proteasome component C5	86.73%	90.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.17%	96.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.76%	96.95%
CHEMBL2581	P07339	Cathepsin D	83.16%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.44%	93.99%

Plants that contains it

• Uvaria mocoli

Cross-Links

• PubChem: 15380424
• LOTUS: LTS0115507
• wikiData: Q105344020