Phlorizin

Details

• Internal ID: 6ee8743b-dc88-4869-a56e-42d61933a928
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: 1-[2,4-dihydroxy-6-[(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=C2OC3C(C(C(C(O3)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](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/t16-,18-,19+,20-,21-/m1/s1
• InChI Key: IOUVKUPGCMBWBT-QNDFHXLGSA-N
• Popularity: 3,234 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

• Phloridzin
• 60-81-1
• Phlorhizin
• Phlorizoside
• Floridzin
• Phlorrhizin
• Phloretin 2'-glucoside
• Phloridzosid
• Phlorrhizen
• Phlorizine
• Phloridzinum
• NSC 2833
• Phloretin-2'-O-beta-glucoside
• Phlorizin hydrate
• AI3-19835
• 7061-54-3
• Phloridzin dihydrate
• EINECS 200-487-1
• Phloretin-2'-beta-glucoside
• UNII-CU9S17279X
• 1-[2-(beta-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
• CHEBI:8113
• CHEMBL245067
• Phloretin-2'-O-.beta.-glucoside
• CU9S17279X
• NSC-2833
• 2'-(beta-D-Glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone
• 1-Propanone, 1-(2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl)-3-(4-hydroxyphenyl)-
• 1-(2,4-dihydroxy-6-(((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-(2,4-dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one
• Phlorizin, dihydrate
• Phlorizin (dihydrate)
• phloretin 2'-O-glucoside
• Phloridzin dihydrate [MI]
• 4,6-dihydroxy-2-(beta-D-glucosido)-beta-(p-hydroxyphenyl)propiophenone
• 1-Propanone, 1-[2-(beta-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
• 2'-(.beta.-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone
• Phloretin-2'-O-glucoside
• SR-01000781913
• Lopin
• 1-Propanone, 1-[2-(.beta.-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
• O-glucoside, 1
• 1-PROPANONE, 1-(2-(.BETA.-D-GLUCOPYRANOSYLOXY)-4,6-DIHYDROXYPHENYL)-3-(4-HYDROXYPHENYL)-
• C21H24O10
• Phlorizin (Phloridzin)
• Spectrum_001291
• PHLORIDZIN [MI]
• SpecPlus_000325
• Spectrum2_000701
• Spectrum3_001227
• Spectrum4_001651
• Spectrum5_000521
• PHLORIDZIN [INCI]
• D06WAL
• PHLORIDZINUM [HPUS]
• PHLORIDZIN [WHO-DD]
• SCHEMBL17290
• BSPBio_002674
• KBioGR_002141
• KBioSS_001771
• SPECTRUM300547
• JMC511145 Compound 1
• DivK1c_006421
• SPBio_000881
• GTPL4757
• DTXSID3075339
• BDBM20875
• KBio1_001365
• KBio2_001771
• KBio2_004339
• KBio2_006907
• KBio3_002174
• HMS2090P10
• Phloretin 2'-ss-D-glucopyranoside
• HY-N0143
• CCG-38341
• s2343
• AKOS015920054
• AC-7976
• CS-2013
• SDCCGMLS-0066626.P001
• 1-Propanone,1-[2-(b-D-glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-
• NCGC00142423-01
• NCGC00142423-02
• NCGC00142423-06
• 1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
• 1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one
• 1-{6-[(2S,4S,5S,3R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetrahydr opyran-2-yloxy)]-2,4-dihydroxyphenyl}-3-(4-hydroxyphenyl)propan-1-one
• AS-15724
• LS-123021
• P0248
• C01604
• A836937
• A868885
• Q413105
• Q-100699
• SR-01000781913-2
• SR-01000781913-4
• SR-01000781913-5
• BRD-K73756878-001-02-9
• 1-[2-(.beta.-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
• 1-[2-(?-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
• 1-[2-(ss-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
• 2'-(beta-D-glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenon
• 3,5-dihydroxy-2-[3-(4-hydroxyphenyl)propanoyl]phenyl beta-D-glucopyranoside
• 1-(2,4-dihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)phenyl)-3-(4-hydroxyphenyl)propan-1-one
• 1-[2,4-dihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-phenyl]-3-(4-hydroxyphenyl)propan-1-one dihydrate;Phlorizin dihydrate
• 112318-65-7

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
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	35481.3 nM	Potency	via CMAUP
CHEMBL2409	P34913	Epoxide hydratase	41720 nM	IC50	PMID: 24679441
CHEMBL1770047	Q9NY91	Low affinity sodium-glucose cotransporter	16 nM; 16 nM	IC50; IC50	PMID: 21873071; via Super-PRED
CHEMBL4979	P13866	Sodium/glucose cotransporter 1	185 nM; 190 nM; 190 nM; 246 nM; 210 nM; 200 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 22889351; PMID: 22652255; PMID: 21873071; PMID: 20302302; PMID: 19785435; PMID: 17374486
CHEMBL3884	P31639	Sodium/glucose cotransporter 2	100 nM; 58.6 nM; 38 nM; 16.4 nM; 16 nM; 36 nM; 27.8 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 17374486; PMID: 24556379; PMID: 23062824; PMID: 22889351; PMID: 22652255; PMID: 21398124; PMID: 20302302
CHEMBL5707	Q9HAS3	Solute carrier family 28 member 3	16000 nM	Ki	PMID: 19097778

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

• Alkanna cappadocica
• Alstonia rostrata
• Artemisia rupestris subsp. rupestris
• Asteriscus aquaticus
• Atalantia racemosa
• Balanophora involucrata
• Betula pendula subsp. mandshurica
• Buddleja cordata
• Capparis spinosa var. ovata
• Charpentiera obovata
• Cinnamomum subavenium
• Crambe tatarica
• Croton montevidensis
• Cynomorium coccineum subsp. songaricum
• Datisca glomerata
• Dioscorea olfersiana
• Diospyros eriantha
• Ecballium elaterium
• Elaeodendron papillosum
• Engelhardia serrata
• Euphorbia humifusa
• Fragaria × ananassa
• Fritillaria monantha
• Helichrysum auriceps
• Hoffmannia strigillosa
• Hubertia tomentosa
• Humulus lupulus
• Kalmia latifolia
• Leionema dentatum
• Ligustrum obtusifolium
• Lippia origanoides
• Litchi chinensis
• Lithocarpus litseifolius
• Lithocarpus pachyphyllus
• Lithocarpus polystachyus
• Lotus ucrainicus
• Malus doumeri
• Malus pumila
• Malus sylvestris
• Millettia erythrocalyx
• Myristica cagayanensis
• Myrsine lancifolia
• Nothofagus fusca
• Ononis vaginalis
• Phyllanthus oligospermus
• Pieris floribunda
• Pieris japonica
• Polygonum pubescens
• Posidonia oceanica
• Prunus domestica
• Pseudowintera colorata
• Pteris semipinnata
• Punica granatum
• Quercus imbricaria
• Rubus idaeus
• Salvia hispanica
• Scorzonera pseudodivaricata
• Scrophularia koelzii
• Solanum aethiopicum
• Spiracantha cornifolia
• Stenocereus griseus
• Syncarpia hillii
• Toxicodendron vernicifluum
• Vaccinium macrocarpon
• Vincetoxicum tanakae
• Vitis vinifera

Cross-Links

• PubChem: 6072
• NPASS: NPC259182
• ChEMBL: CHEMBL245067
• LOTUS: LTS0207095
• wikiData: Q105346485