1-[2,4-Dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one

Details

• Internal ID: 05275c5d-8bfc-4d85-95cf-3e3ba50371c1
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 1-[2,4-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
• SMILES (Canonical): C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2
• InChI Key: IOUVKUPGCMBWBT-UHFFFAOYSA-N
• Popularity: 192 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₁₀
• Molecular Weight: 436.40 g/mol
• Exact Mass: 436.13694696 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): -0.20
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• NSC2833
• Phloretin-2'-O-glucoside
• Phloridizin
• CHEMBL45266
• SCHEMBL113699
• SCHEMBL22022720
• CHEBI:182131
• IOUVKUPGCMBWBT-UHFFFAOYSA-N
• BDBM237198
• HMS3656K07
• BCP29914
• LMPK12120517
• MFCD00006591
• 1-[2,4-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
• NCI60_002323
• SY030366
• FT-0603255
• 1-Propanone,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7510	75.10%
Caco-2	-	0.8979	89.79%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.7630	76.30%
OATP2B1 inhibitior	-	0.5582	55.82%
OATP1B1 inhibitior	+	0.9017	90.17%
OATP1B3 inhibitior	+	0.9011	90.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.5619	56.19%
P-glycoprotein inhibitior	-	0.6035	60.35%
P-glycoprotein substrate	-	0.8331	83.31%
CYP3A4 substrate	+	0.5601	56.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.8751	87.51%
CYP2C9 inhibition	+	0.5454	54.54%
CYP2C19 inhibition	-	0.8258	82.58%
CYP2D6 inhibition	-	0.9235	92.35%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	+	0.7505	75.05%
CYP inhibitory promiscuity	-	0.7838	78.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7465	74.65%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8117	81.17%
Skin irritation	-	0.8164	81.64%
Skin corrosion	-	0.9629	96.29%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4454	44.54%
Micronuclear	-	0.6067	60.67%
Hepatotoxicity	-	0.8301	83.01%
skin sensitisation	-	0.8315	83.15%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.7793	77.93%
Acute Oral Toxicity (c)	III	0.7398	73.98%
Estrogen receptor binding	+	0.7219	72.19%
Androgen receptor binding	+	0.5416	54.16%
Thyroid receptor binding	-	0.5352	53.52%
Glucocorticoid receptor binding	-	0.5465	54.65%
Aromatase binding	+	0.5628	56.28%
PPAR gamma	+	0.6841	68.41%
Honey bee toxicity	-	0.7546	75.46%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5855	58.55%
Fish aquatic toxicity	+	0.6914	69.14%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1770047	Q9NY91	Low affinity sodium-glucose cotransporter	16 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.22%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.77%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.28%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.33%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.90%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	90.46%	94.73%
CHEMBL3194	P02766	Transthyretin	89.02%	90.71%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.08%	86.92%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.06%	96.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.53%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.50%	89.00%
CHEMBL4208	P20618	Proteasome component C5	86.39%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.91%	95.50%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	85.69%	85.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.55%	86.33%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.66%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	84.45%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.26%	95.56%

Plants that contains it

• Eucalyptus globulus
• Kalmia procumbens
• Lippia origanoides
• Litchi chinensis
• Lithocarpus litseifolius
• Lithocarpus polystachyus
• Malus doumeri
• Malus pumila
• Pieris japonica
• Prunus domestica
• Punica granatum

Cross-Links

• PubChem: 4789
• LOTUS: LTS0176319
• wikiData: Q105116909