Trilobatin

Details

• Internal ID: 8643b9d7-1303-4803-a6d3-ac3cf0fc1e7a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-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=C2O)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
• InChI Key: GSTCPEBQYSOEHV-QNDFHXLGSA-N
• Popularity: 22 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

• 4192-90-9
• p-Phlorizin
• p-Phloridzin
• CHEMBL514177
• UNII-23298I791N
• 23298I791N
• 1-Propanone, 1-(4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
• 1-[2,6-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
• phloretin-4'-O-glucoside
• PRUNINDIHYDROCHALCONE
• phloretin-4'-beta-D-glucoside
• phloretin 4'-glucoside
• Phloretin-4-O-glucoside
• PHLORIZIN, P-
• PRUNIN DIHYDROCHALCONE
• MEGxp0_002006
• SCHEMBL1144758
• FEMA NO. 4674
• ACon1_000618
• DTXSID10194681
• CHEBI:145829
• HY-N4100
• phloretin-4'-beta-D-glucopyranoside
• BDBM50256748
• s9064
• 3,5-dihydroxy-4-[3-(4-hydroxyphenyl)propanoyl]phenyl beta-D-glucopyranoside
• AKOS032948098
• CCG-269084
• NCGC00168907-01
• PHLORETIN 4'-.BETA.-D-GLUCOSIDE
• AC-34712
• AS-82792
• CS-0032106
• Q3539189
• BRD-K75748852-001-01-6
• Z3251695350
• 1-(4-(beta-D-glucopyranosyloxy)-2,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1-propanone
• 1-(2,6-dihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one
• 1-(2,6-dihydroxy-4-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one
• 1-PROPANONE, 1-(4-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,6-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	-	0.9003	90.03%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7630	76.30%
OATP2B1 inhibitior	-	0.5579	55.79%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9011	90.11%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.7220	72.20%
P-glycoprotein substrate	-	0.8822	88.22%
CYP3A4 substrate	+	0.5373	53.73%
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	+	0.6399	63.99%
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	-	0.8172	81.72%
Skin irritation	-	0.8164	81.64%
Skin corrosion	-	0.9629	96.29%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3917	39.17%
Micronuclear	-	0.6067	60.67%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8315	83.15%
Respiratory toxicity	-	0.7667	76.67%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	-	0.8240	82.40%
Acute Oral Toxicity (c)	III	0.7398	73.98%
Estrogen receptor binding	+	0.7819	78.19%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.5193	51.93%
Glucocorticoid receptor binding	-	0.4870	48.70%
Aromatase binding	+	0.6144	61.44%
PPAR gamma	+	0.7740	77.40%
Honey bee toxicity	-	0.7312	73.12%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.6914	69.14%

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	98.46%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.38%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.56%	99.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.74%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.55%	98.95%
CHEMBL3437	Q16853	Amine oxidase, copper containing	88.13%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.08%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	87.54%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.35%	94.00%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	86.34%	85.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	86.16%	94.62%
CHEMBL4208	P20618	Proteasome component C5	84.94%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.56%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.53%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.96%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.89%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.80%	96.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.46%	95.50%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.14%	99.15%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.98%	95.89%
CHEMBL3194	P02766	Transthyretin	80.57%	90.71%

Plants that contains it

• Balanophora harlandii
• Balanophora tobiracola
• Eriolobus trilobatus
• Lithocarpus litseifolius
• Lithocarpus pachyphyllus
• Lithocarpus polystachyus
• Mentha canadensis
• Vitis saccharifera
• Vitis vinifera

Cross-Links

• PubChem: 6451798
• NPASS: NPC121001
• LOTUS: LTS0037546
• wikiData: Q3539189