Phlorizin (BioCAD00000016204)

plant natural products microbial natural products

Metabolite Card

Formula: C21H24O10 (436.1369)
SMILES: OC[C@H]1O[C@@H](OC2=CC(O)=CC(O)=C2C(=O)CCC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

Synonyms [en]

Phloridzin; Phlorizin; Phlorhizin; Phloretin 2'-glucoside; Floridzin; Phlorizoside

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Phlorizin. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000016204). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Phlorizin, also known as phlorizoside or phlorrhizen, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Phlorizin (also referred to as phloridzin; chemical name phloretin-2'-‚âà√≠‚Äö√¢¬ß-D-glucopyranoside) is a glucoside of phloretin, a dihydrochalcone, a family of bicyclic flavonoids, which in turn is a subgroup in the diverse phenylpropanoid synthesis pathway in plants. In humans, phlorizin is involved in lactose degradation. Phlorizin is a bitter tasting compound. phlorizin is found, on average, in the highest concentration in a few different foods, such as mexican oregano, european plums, and apples and in a lower concentration in pomegranates and apricots. phlorizin has also been detected, but not quantified, in several different foods, such as epazotes, durians, chinese broccoli, sesames, and sweet potato. This could make phlorizin a potential biomarker for the consumption of these foods. It is of sweet taste and contains four molecules of water in the crystal. Phlorizin is found primarily in unripe Malus (apple), root bark of apple, trace amounts have been found in strawberry. It is poorly soluble in ether and cold water, but soluble in ethanol and hot water. Closely related species, such as pear (Pyrus communis), cherry, and other fruit trees in the Rosaceae do not contain phloridzin. Phlorizin was studied as a potential pharmaceutical treatment for type 2 diabetes, but has since been superseded by more selective and more promising synthetic analogs, such as empagliflozin, canagliflozin and dapagliflozin. Phlorizin is a competitive inhibitor of SGLT1 and SGLT2 because it competes with D-glucose for binding to the carrier; this reduces renal glucose transport, lowering the amount of glucose in the blood. Phlorizin is not an effective drug because when orally consumed, it is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine. Above 200 °C, it decomposes.

Cytoplasm Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 112318-65-7
  • CAS Registry Number: 4192-90-9
  • CAS Registry Number: 60-81-1
  • CAS Registry Number: 60-81-1 112318-65-7 16055-86-0 52276-56-9
  • CAS Registry Number: 7061-54-3
  • PubChem: 4789
  • PubChem: 6072
  • ChEBI: ChEBI:182131
  • ChEBI: ChEBI:8113
  • HMDB: HMDB0036634
  • HMDB: HMDB36634
  • LipidMaps: LMPK12120517
  • KEGG: C01604
  • BioCyc: CPD-12447
  • NCBI MeSH: Phlorhizin
  • Wikipedia: Phlorizin
  • DrugBank: DB16771
  • RefMet: RM0136687
  • MoNA: BML00588
  • MoNA: BML00593
  • MoNA: BML00598
  • MoNA: BML81935
  • MoNA: BML81936
  • MoNA: BML81938
  • MoNA: Bruker_HCD_library000711
  • MoNA: CE000071
  • MoNA: CE000072
  • MoNA: CE000073
  • MoNA: CE000074
  • MoNA: CE000075
  • MoNA: MoNA035270
  • MoNA: MoNA035271
  • MoNA: MoNA035274
  • MoNA: MoNA038252
  • MoNA: MoNA_0001590
  • MoNA: MoNA_0001591
  • MoNA: MoNA_0001592
  • MoNA: MoNA_0001593
  • MoNA: MoNA_0001594
  • MoNA: MoNA_0001597
  • MoNA: MoNA_0001600
  • MoNA: MoNA_0001601
  • MoNA: MoNA_0007008
  • MoNA: MoNA_0007009
  • MoNA: MoNA_0007010
  • MoNA: MoNA_0007011
  • MoNA: MoNA_0007012
  • MoNA: MoNA_0007028
  • MoNA: MoNA_0007228
  • MoNA: MoNA_0007229
  • MoNA: MoNA_0007231
  • MoNA: MoNA_0007352
  • MoNA: MoNA_0007353
  • MoNA: MoNA_0008726
  • MoNA: MoNA_0008727
  • MoNA: MoNA_0008728
  • MoNA: MoNA_0008729
  • MoNA: MoNA_0008730
  • MoNA: MoNA_0008731
  • MoNA: MoNA_0008966
  • MoNA: MoNA_0008967
  • MoNA: MoNA_0008968
  • MoNA: MoNA_0008969
  • MoNA: MoNA_0009144
  • MoNA: MoNA_0009145
  • MoNA: MoNA_0009146
  • MoNA: MoNA_0009147
  • MoNA: MoNA_0009150
  • MoNA: MoNA_0009151
  • MoNA: MoNA_0009390
  • MoNA: MoNA_0009391
  • MoNA: MoNA_0009392
  • MoNA: MoNA_0009393
  • MoNA: MoNA_0009394
  • MoNA: MoNA_0009396
  • MoNA: MoNA_0009657
  • MoNA: MoNA_0009658
  • MoNA: MoNA_0009659
  • MoNA: MoNA_0009660
  • MoNA: MoNA_0009661
  • MoNA: MoNA_0009662
  • MoNA: MoNA_0009663
  • MoNA: PB006207
  • MoNA: PB006208
  • MoNA: PB006209
  • MoNA: PR020074
  • MoNA: PR309445
  • MoNA: PS086401
  • MoNA: PS086402
  • MoNA: PS086403
  • MoNA: PS086404
  • MoNA: PS086405
  • MoNA: PS086406
  • MoNA: PS086407
  • MoNA: PS086408
  • MoNA: PS086409
  • MoNA: PS086410
  • MoNA: PS086411
  • MoNA: RIKENPlaSMA006434
  • MoNA: RIKENPlaSMA006439
  • MoNA: RIKENPlaSMA006444
  • MoNA: RIKENPlaSMA006449
  • MoNA: RIKENPlaSMA006454
  • MoNA: RIKENPlaSMA006459
  • MoNA: RIKENPlaSMA006464
  • MoNA: RIKENPlaSMA006469
  • MoNA: RIKENPlaSMA006474
  • MoNA: RIKENPlaSMA006479
  • MoNA: RIKENPlaSMA006484
  • MoNA: RIKENPlaSMA006489
  • MoNA: VF-NPL-LTQ001957
  • MoNA: VF-NPL-LTQ001958
  • MoNA: VF-NPL-QEHF005032
  • MoNA: VF-NPL-QEHF005033
  • MoNA: VF-NPL-QEHF005034
  • MoNA: VF-NPL-QEHF005035
  • MoNA: VF-NPL-QEHF005036
  • MoNA: VF-NPL-QEHF005037
  • MoNA: VF-NPL-QEHF005038
  • MoNA: VF-NPL-QEHF005039
  • MoNA: VF-NPL-QEHF005040
  • MoNA: VF-NPL-QEHF005041
  • MoNA: VF-NPL-QEHF005042
  • MoNA: VF-NPL-QEHF005043
  • MoNA: VF-NPL-QEHF005044
  • MoNA: VF-NPL-QEHF005045
  • MoNA: VF-NPL-QEHF005046
  • MoNA: VF-NPL-QTOF009277
  • MoNA: VF-NPL-QTOF009278
  • MoNA: VF-NPL-QTOF009279
  • MoNA: VF-NPL-QTOF009280
  • MoNA: VF-NPL-QTOF009281
  • MoNA: VF-NPL-QTOF009282
  • MoNA: VF-NPL-QTOF009283
  • MoNA: VF-NPL-QTOF009284
  • Metlin: METLIN_3535
  • Coconut NaturalProduct: CNP0290030.2
  • Coconut NaturalProduct: CNP0290030.4
  • Coconut NaturalProduct: CNP0290030.5
  • Coconut NaturalProduct: CNP0290030.6
  • Coconut NaturalProduct: CNP0328345.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R12088 2.4.1.357 UDP-alpha-D-glucose:phloretin 2'-O-D-glucosyltransferase
Rhea:RHEA:51577 2.4.1.357 phloretin + UDP-α-D-glucose => phlorizin + UDP + H+
Rhea:RHEA:51578 2.4.1.357 phlorizin + UDP + H+ => phloretin + UDP-α-D-glucose
Rhea:RHEA:51579 2.4.1.357 phloretin + UDP-α-D-glucose <=> phlorizin + UDP + H+
Rhea:RHEA:69640 phlorizin + H2O => phloretin + β-D-glucose
Rhea:RHEA:69641 phloretin + β-D-glucose => phlorizin + H2O
Rhea:RHEA:69642 phlorizin + H2O <=> phloretin + β-D-glucose
BioCyc:RXN-11465 2.4.1.357 CPD-12575 + PHLORETIN --> CPD-12447 + UDP
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Organism Source

Taxonomy Source

  1. Agastache rugosa [ncbi taxid: 39271]
  2. Agave salmiana [ncbi taxid: 332343]
  3. Alkanna cappadocica [ncbi taxid: 2650392]
  4. Aloe hijazensis [ncbi taxid: ]
  5. Aloe vera [ncbi taxid: 34199]
  6. Alstonia undulifolia [ncbi taxid: ]
  7. Artemisia dentata [ncbi taxid: ]
  8. Asteriscus aquaticus [ncbi taxid: 73982]
  9. Atalantia racemosa [ncbi taxid: 159026]
  10. Balanophora involucrata [ncbi taxid: 2894844]
  11. Betula platyphylla [ncbi taxid: 78630]
  12. Boehmeria tricuspis [ncbi taxid: 644073]
  13. Botryosphaeria berengeriana [ncbi taxid: 509207]
  14. Buddleja cordata [ncbi taxid: 168492]
  15. Buphane fischeri [ncbi taxid: ]
  16. Capparis ovata [ncbi taxid: ]
  17. Cassine papillosa [ncbi taxid: ]
  18. Centaurea malacitana [ncbi taxid: ]
  19. Charpentiera obovata [ncbi taxid: 240039]
  20. Cinnamomum subavenium [ncbi taxid: 977953]
  21. Clathria prolifera [ncbi taxid: 1190602]
  22. Conus pulicarius [ncbi taxid: 93154]
  23. Cordeauxia edulis [ncbi taxid: 191921]
  24. Crambe tatarica [ncbi taxid: 71346]
  25. Croton montevidensis [ncbi taxid: 323071]
  26. Croton tiglium [ncbi taxid: 497687]
  27. Datisca glomerata [ncbi taxid: 34297]
  28. Dioscorea olfersiana [ncbi taxid: 1933803]
  29. Diospyros eriantha [ncbi taxid: 1009467]
  30. Ecballium elaterium [ncbi taxid: 3679]
  31. Echinus microtuberculatus [ncbi taxid: ]
  32. Erythrina americana [ncbi taxid: 932743]
  33. Eucalyptus globulus [ncbi taxid: 34317]
  34. Euphorbia humifusa [ncbi taxid: 212301]
  35. Fagus fusca [ncbi taxid: ]
  36. Flemingia strobilifera [ncbi taxid: 634992]
  37. Fritillaria ningguoensis [ncbi taxid: ]
  38. Gracilaria corticata [ncbi taxid: 223959]
  39. Helichrysum auriceps [ncbi taxid: 1442641]
  40. Hoffmannia strigillosa [ncbi taxid: ]
  41. Hubertia tomentosa [ncbi taxid: 462449]
  42. Humulus lupulus [ncbi taxid: 3486]
  43. Iotrochota purpurea [ncbi taxid: ]
  44. Juniperus rigida var. conferta [ncbi taxid: 13102]
  45. Kalmia latifolia [ncbi taxid: 45902]
  46. Lemaireocereus griseus [ncbi taxid: ]
  47. Lepidium sativum [ncbi taxid: 33125]
  48. Ligustrum obtusifolium [ncbi taxid: 178760]
  49. Lippia graveolens [ncbi taxid: 1986359]
  50. Litchi chinensis [ncbi taxid: 151069]
  51. Lotus ucrainicus [ncbi taxid: 1006353]
  52. Malus domestica [ncbi taxid: 3750]
  53. Malus pumila [ncbi taxid: 283210]
  54. Metridium senile [ncbi taxid: 6116]
  55. Millettia erythrocalyx [ncbi taxid: 1679271]
  56. Mycobacterium leprae [ncbi taxid: 1769]
  57. Myelobia smerintha [ncbi taxid: ]
  58. Myristica cagayanensis [ncbi taxid: ]
  59. Negombata magnifica [ncbi taxid: 344322]
  60. Ocotea puberula [ncbi taxid: 489023]
  61. Ononis vaginalis [ncbi taxid: 798051]
  62. Ophidiaster ophidianus [ncbi taxid: 232926]
  63. Paeonia rockii [ncbi taxid: 62886]
  64. Phebalium dentatum [ncbi taxid: ]
  65. Phyllanthus oligospermus [ncbi taxid: ]
  66. Pieris japonica [ncbi taxid: 317406]
  67. Polygonum flaccidum [ncbi taxid: 2899266]
  68. Prorocentrum micans [ncbi taxid: 2945]
  69. Prunus armeniaca [ncbi taxid: 36596]
  70. Prunus domestica [ncbi taxid: 3758]
  71. Pseudowintera colorata [ncbi taxid: 22294]
  72. Pteris semipinnata [ncbi taxid: 265705]
  73. Punica granatum [ncbi taxid: 22663]
  74. Quercus imbricaria [ncbi taxid: 39469]
  75. Rapanea lancifolia [ncbi taxid: ]
  76. Rubus idaeus [ncbi taxid: 32247]
  77. Salvia hispanica [ncbi taxid: 49212]
  78. Scorzonera pseudodivaricata [ncbi taxid: ]
  79. Scrophularia koelzii [ncbi taxid: 1970701]
  80. Solanum aethiopicum [ncbi taxid: 205524]
  81. Solanum andigena [ncbi taxid: ]
  82. Spiracantha cornifolia [ncbi taxid: 1136794]
  83. Streptomyces platensis [ncbi taxid: 58346]
  84. Symplocos lancifolia [ncbi taxid: 239704]
  85. Syncarpia hillii [ncbi taxid: 271921]
  86. Toxicodendron vernicifluum [ncbi taxid: 4013]
  87. Tylophora tanakae [ncbi taxid: ]
  88. Viviparus japonicus [ncbi taxid: ]
  89. Xenoacremonium recifei [ncbi taxid: 1036759]
  90. Flemingia strobilifera [ncbi taxid: 634992]
  91. Kalmia latifolia [ncbi taxid: 45902]
  92. Litchi chinensis [ncbi taxid: 151069]
  93. Lithocarpus liseifolius [ncbi taxid: ]
  94. Lithophragma affine [ncbi taxid: 40793]
  95. Loiseleuria procumbens (L.) Desv. [ncbi taxid: ]
  96. Malus doumeri varl formosana [ncbi taxid: ]
  97. Malus spp. [ncbi taxid: ]
  98. Pieris japonica [ncbi taxid: 317406]
  99. Rhododendron spp. [ncbi taxid: ]
  100. Symplocos lancifolia [ncbi taxid: 239704]
  101. Symplocos spicata [ncbi taxid: ]
  102. Allophyllum divaricatum [ncbi taxid: 66233]
  103. Aplysia fasciata [ncbi taxid: 144767]
  104. Aspergillus fischeri [ncbi taxid: 36630]
  105. Bazzania trilobata [ncbi taxid: 13808]
  106. Bulgaria pura [ncbi taxid: ]
  107. Capnophyllum dichotomum [ncbi taxid: 52454]
  108. Dendrodoris grandiflora [ncbi taxid: 1798229]
  109. Eupomatia bennettii [ncbi taxid: 13521]
  110. Guettarda grazielae [ncbi taxid: ]
  111. Haematomma coccineum [ncbi taxid: ]
  112. Helichrysum decumbens [ncbi taxid: ]
  113. Mentha canadensis [ncbi taxid: 294733]
  114. Metrosideros polymorpha [ncbi taxid: 101976]
  115. Piliostigma reticulatum [ncbi taxid: 228531]
  116. Psilocybe semilanceata [ncbi taxid: 181775]
  117. Solandra grandiflora [ncbi taxid: 33123]
  118. Solanum erianthum [ncbi taxid: 374041]
  119. Streptomyces alanosinicus [ncbi taxid: 68171]
  120. Supella longipalpa [ncbi taxid: 83902]
  121. Tinospora sinensis [ncbi taxid: 152349]
  122. Usnea longissima [ncbi taxid: ]
  123. Vitis piasezkii [ncbi taxid: 228411]
  124. Zanthoxylum tingoassuiba [ncbi taxid: 2099546]

Pathway Synthetic

pathway id name
PlantCyc:SPIRODELA_PWY-6515 phloridzin biosynthesis
PlantCyc:SVIRIDIS_PWY-6515 phloridzin biosynthesis
PlantCyc:AMBORELLA_PWY-6515 phloridzin biosynthesis
PlantCyc:RUBBERTREE_PWY-6515 phloridzin biosynthesis
PlantCyc:CORN_PWY-6515 phloridzin biosynthesis
PlantCyc:VALLEYOAK_PWY-6515 phloridzin biosynthesis
PlantCyc:OMERIDIONALIS_PWY-6515 phloridzin biosynthesis
PlantCyc:FVESCA_VESCA_PWY-6515 phloridzin biosynthesis
PlantCyc:MPOLYMORPHA_PWY-6515 phloridzin biosynthesis
PlantCyc:MSINENSIS_PWY-6515 phloridzin biosynthesis
PlantCyc:OBRACHYANTHA_PWY-6515 phloridzin biosynthesis
PlantCyc:CARROT_PWY-6515 phloridzin biosynthesis
PlantCyc:PHALLII_PWY-6515 phloridzin biosynthesis
PlantCyc:OILPALM_PWY-6515 phloridzin biosynthesis
PlantCyc:REDSAGE_PWY-6515 phloridzin biosynthesis
PlantCyc:SORGHUMBICOLOR_PWY-6515 phloridzin biosynthesis
PlantCyc:SUNFLOWER_PWY-6515 phloridzin biosynthesis
PlantCyc:SWITCHGRASS_PWY-6515 phloridzin biosynthesis
PlantCyc:WHEATA_PWY-6515 phloridzin biosynthesis
PlantCyc:WHEATD_PWY-6515 phloridzin biosynthesis
View All Pathways