(1R)-1-hydroxy-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)propan-2-one

Details

• Internal ID: 8fc88c4d-f862-4283-ade0-ba68ea0636e4
• Taxonomy: Phenylpropanoids and polyketides > Linear 1,3-diarylpropanoids > Cinnamylphenols
• IUPAC Name: (1R)-1-hydroxy-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)propan-2-one
• InChI: InChI=1S/C16H16O5/c1-21-15-9-12(18)6-7-13(15)16(20)14(19)8-10-2-4-11(17)5-3-10/h2-7,9,16-18,20H,8H2,1H3/t16-/m1/s1
• InChI Key: BAVJPTQBNBQJFK-MRXNPFEDSA-N
• Popularity: 2 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: 1.80
• Atomic LogP (AlogP): 1.95
• 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	+	0.9844	98.44%
Caco-2	+	0.7977	79.77%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8832	88.32%
OATP2B1 inhibitior	-	0.7205	72.05%
OATP1B1 inhibitior	+	0.9092	90.92%
OATP1B3 inhibitior	+	0.9346	93.46%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7359	73.59%
P-glycoprotein inhibitior	-	0.7884	78.84%
P-glycoprotein substrate	-	0.7505	75.05%
CYP3A4 substrate	-	0.5197	51.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4096	40.96%
CYP3A4 inhibition	-	0.8414	84.14%
CYP2C9 inhibition	-	0.6471	64.71%
CYP2C19 inhibition	+	0.7716	77.16%
CYP2D6 inhibition	-	0.8368	83.68%
CYP1A2 inhibition	+	0.8335	83.35%
CYP2C8 inhibition	+	0.5833	58.33%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8143	81.43%
Carcinogenicity (trinary)	Non-required	0.6395	63.95%
Eye corrosion	-	0.9523	95.23%
Eye irritation	+	0.8119	81.19%
Skin irritation	-	0.6858	68.58%
Skin corrosion	-	0.9518	95.18%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5679	56.79%
Micronuclear	+	0.6577	65.77%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8471	84.71%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.7234	72.34%
Acute Oral Toxicity (c)	III	0.6969	69.69%
Estrogen receptor binding	+	0.7485	74.85%
Androgen receptor binding	+	0.5293	52.93%
Thyroid receptor binding	+	0.7025	70.25%
Glucocorticoid receptor binding	+	0.7586	75.86%
Aromatase binding	+	0.5570	55.70%
PPAR gamma	-	0.5509	55.09%
Honey bee toxicity	-	0.9110	91.10%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9126	91.26%

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	97.85%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.90%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.72%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	92.42%	90.20%
CHEMBL2535	P11166	Glucose transporter	92.24%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.29%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.21%	94.45%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	89.69%	95.89%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.95%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.70%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.56%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.33%	96.95%
CHEMBL4208	P20618	Proteasome component C5	84.94%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.66%	95.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.61%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.06%	94.00%

Plants that contains it

• Xanthocercis zambesiaca

Cross-Links

• PubChem: 86310826
• LOTUS: LTS0154872
• wikiData: Q104922463