Phloretin (BioCAD00000016201)

blood urine fibroblasts intestine platelet plant natural products microbial natural products

Metabolite Card

Formula: C15H14O5 (274.0841)
SMILES: OC1=CC=C(CCC(=O)C2=C(O)C=C(O)C=C2O)C=C1

Synonyms [en]

phloretin; 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one; Phloretol; 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone; Dihydronaringenin; beta-(p-Hydroxyphenyl)phloropropiophenone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Phloretin. 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: BioCAD00000016201). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Phloretin is the aglucone of phlorizin, a plant-derived dihydrochalcone phytochemical reported to promote potent antioxidative activities in peroxynitrite scavenging and the inhibition of lipid peroxidation. Phloretin, which is present in apples, pears and tomatoes, has been found to inhibit the growth of several cancer cells and induce apoptosis of B16 melanoma and HL60 human leukemia cells. Phloretin also inhibits HT-29 cell growth by inducing apoptosis, which may be mediated through changes in mitochondrial membrane permeability and activation of the caspase pathways. Phloretin is a well-known inhibitor of eukaryotic urea transporters, blocks VacA-mediated urea and ion transport (PMID:18158826, 11560962, 18063724, 15671209, 12083758). Phloretin is a biomarker for the consumption of apples. Phloretin has been found to be a metabolite of Escherichia (PMID:23542617).

Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 137987-87-2
  • CAS Registry Number: 35274-53-4
  • CAS Registry Number: 59058-14-9
  • CAS Registry Number: 60-82-2
  • CAS Registry Number: Phloretin - CAS 60-82-2
  • PubChem: 4788
  • ChEBI: ChEBI:17276
  • HMDB: HMDB0003306
  • LipidMaps: LMPK12120525
  • KEGG: C00774
  • BioCyc: PHLORETIN
  • NCBI MeSH: Phloretin
  • Wikipedia: Phloretin
  • DrugBank: DB07810
  • RefMet: RM0135273
  • MoNA: BML00573
  • MoNA: BML00579
  • MoNA: BML00585
  • MoNA: BML00590
  • MoNA: BML00595
  • MoNA: BML00600
  • MoNA: BML81930
  • MoNA: BML81931
  • MoNA: BML81932
  • MoNA: BML81933
  • MoNA: FiehnHILIC000682
  • MoNA: FiehnHILIC001443
  • MoNA: FiehnHILIC002251
  • MoNA: FiehnHILIC002928
  • MoNA: FiehnLib000836
  • MoNA: HMDB0003306_c_ms_99802
  • MoNA: HMDB0003306_ms_ms_2233
  • MoNA: HMDB0003306_ms_ms_2234
  • MoNA: HMDB0003306_ms_ms_2235
  • MoNA: MoNA_0001584
  • MoNA: MoNA_0001585
  • MoNA: MoNA_0001586
  • MoNA: MoNA_0001587
  • MoNA: MoNA_0001588
  • MoNA: MoNA_0001589
  • MoNA: PB000681
  • MoNA: PB000682
  • MoNA: PB000701
  • MoNA: PB000702
  • MoNA: TY000156
  • MoNA: TY000157
  • MoNA: TY000158
  • MoNA: VF-NPL-LTQ000079
  • MoNA: VF-NPL-LTQ000080
  • MoNA: VF-NPL-LTQ000081
  • MoNA: VF-NPL-LTQ000082
  • MoNA: VF-NPL-QEHF000145
  • MoNA: VF-NPL-QEHF000146
  • MoNA: VF-NPL-QEHF000147
  • MoNA: VF-NPL-QEHF000148
  • MoNA: VF-NPL-QEHF000149
  • MoNA: VF-NPL-QEHF000150
  • MoNA: VF-NPL-QTOF009271
  • MoNA: VF-NPL-QTOF009272
  • MoNA: VF-NPL-QTOF009273
  • MoNA: VF-NPL-QTOF009274
  • MoNA: VF-NPL-QTOF009275
  • MoNA: VF-NPL-QTOF009276
  • Metlin: METLIN_3405
  • Coconut NaturalProduct: CNP0048959.0
  • Coconut NaturalProduct: CNP0090039.0
  • Coconut NaturalProduct: CNP0212159.0
  • Coconut NaturalProduct: CNP0243919.0
  • Coconut NaturalProduct: CNP0266115.0
  • Coconut NaturalProduct: CNP0314598.0
  • Coconut NaturalProduct: CNP0324171.0
  • Coconut NaturalProduct: CNP0377493.0
  • Coconut NaturalProduct: CNP0379475.0
  • Coconut NaturalProduct: CNP0565118.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02901 3.7.1.4 phloretin acylhydrolase (phloroglucinol-forming)
KEGG:R12088 2.4.1.357 UDP-alpha-D-glucose:phloretin 2'-O-D-glucosyltransferase
KEGG:R12117 2.3.1.74 malonyl-CoA:dihydro-4-coumaroyl-CoA malonyltransferase(cyclizing)
KEGG:R13073 C00509 + C00004 + C00080<=>C00774 + C00003
Rhea:RHEA:23397 3.7.1.4 phloretin + H2O => phloretate + 1,3,5-trihydroxybenzene + H+
Rhea:RHEA:23398 3.7.1.4 phloretate + 1,3,5-trihydroxybenzene + H+ => phloretin + H2O
Rhea:RHEA:23399 3.7.1.4 phloretin + H2O <=> phloretate + 1,3,5-trihydroxybenzene + H+
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:65149 phloretin + UDP-α-D-glucose => trilobatin + UDP + H+
Rhea:RHEA:65150 trilobatin + UDP + H+ => phloretin + UDP-α-D-glucose
Rhea:RHEA:65151 phloretin + UDP-α-D-glucose <=> trilobatin + 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
BioCyc:RXN-18724 2.4.1.360 CPD-12575 + PHLORETIN --> CPD-20010 + UDP + PROTON
BioCyc:PHLORETIN-HYDROLASE-RXN 3.7.1.4 WATER + PHLORETIN --> PROTON + CPD-16 + PHLORETATE
BioCyc:RXN-11468 2.3.1.74 CPD-12449 + 3 MALONYL-COA + 3 PROTON --> PHLORETIN + 4 CO-A + 3 CARBON-DIOXIDE
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Organism Source

Taxonomy Source

  1. Alkanna cappadocica [ncbi taxid: 2650392]
  2. Amorphophallus konjac [ncbi taxid: 78372]
  3. Aniba santalodora [ncbi taxid: ]
  4. Artemisia dentata [ncbi taxid: ]
  5. Astragalus circassicus [ncbi taxid: ]
  6. Atalantia racemosa [ncbi taxid: 159026]
  7. Beilschmiedia madang [ncbi taxid: ]
  8. Bethencourtia palmensis [ncbi taxid: 462391]
  9. Boesenbergia pandurata [ncbi taxid: ]
  10. Boswellia ovalifoliolata [ncbi taxid: 613108]
  11. Buddleja cordata [ncbi taxid: 168492]
  12. Buphane fischeri [ncbi taxid: ]
  13. Campanula choziatowskyi [ncbi taxid: ]
  14. Centaurea scoparia [ncbi taxid: 2072395]
  15. Centaurea sonchifolia [ncbi taxid: ]
  16. Citrullus lanatus [ncbi taxid: 3654]
  17. Citrus limon [ncbi taxid: ]
  18. Colchicum filifolium [ncbi taxid: 280460]
  19. Crambe tatarica [ncbi taxid: 71346]
  20. Cynoglossum macrostylum [ncbi taxid: 1452877]
  21. Dialium excelsum [ncbi taxid: 1608024]
  22. Diospyros eriantha [ncbi taxid: 1009467]
  23. Drymaria cordata [ncbi taxid: 191453]
  24. Dysidea fragilis [ncbi taxid: 1336851]
  25. Erythrina americana [ncbi taxid: 932743]
  26. Erythrina hypaphorus [ncbi taxid: ]
  27. Esox lucius [ncbi taxid: 8010]
  28. Etmopterus spinax [ncbi taxid: 648166]
  29. Euphorbia hylonoma [ncbi taxid: 526195]
  30. Fritillaria ningguoensis [ncbi taxid: ]
  31. Hardenbergia violacea [ncbi taxid: 53885]
  32. Helichrysum splendidum [ncbi taxid: 261804]
  33. Heliotropium scabrum [ncbi taxid: ]
  34. Helleborus macranthus [ncbi taxid: ]
  35. Hoffmannia strigillosa [ncbi taxid: ]
  36. Homo sapiens [ncbi taxid: 9606]
  37. Humulus lupulus [ncbi taxid: 3486]
  38. Iris kashmiriana [ncbi taxid: ]
  39. Juniperus rigida var. conferta [ncbi taxid: 13102]
  40. Kalmia latifolia [ncbi taxid: 45902]
  41. Lactarius mitissimus [ncbi taxid: 118866]
  42. Lemaireocereus griseus [ncbi taxid: ]
  43. Lemonia spectabilis [ncbi taxid: ]
  44. Lepechinia urbanii [ncbi taxid: 1405049]
  45. Loiseleuria procumbens (L.) Desv. [ncbi taxid: ]
  46. Lonchocarpus chiricanus [ncbi taxid: 1582177]
  47. Maclura cochinchinensis [ncbi taxid: 194324]
  48. Malus domestica [ncbi taxid: 3750]
  49. Malus doumeri varl formosana [ncbi taxid: ]
  50. Malus pumila [ncbi taxid: 283210]
  51. Matricaria sabulosa [ncbi taxid: ]
  52. Matsucoccus josephi [ncbi taxid: ]
  53. Mentzelia decapetala [ncbi taxid: 37834]
  54. Millettia erythrocalyx [ncbi taxid: 1679271]
  55. Mimosa pigra [ncbi taxid: 367322]
  56. Mucuna holtonii [ncbi taxid: 1127093]
  57. Mycobacterium leprae [ncbi taxid: 1769]
  58. Negombata magnifica [ncbi taxid: 344322]
  59. Nepytia freemani [ncbi taxid: 942327]
  60. Ononis vaginalis [ncbi taxid: 798051]
  61. Orgyia pseudotsugata [ncbi taxid: 33414]
  62. Parmotrema nilgherrense [ncbi taxid: 1450753]
  63. Petunia axillaris subsp. parodii [ncbi taxid: 55890]
  64. Pieris japonica [ncbi taxid: 317406]
  65. Podocarpus dacrydioides [ncbi taxid: ]
  66. Populus trichocarpa [ncbi taxid: 3694]
  67. Preussia terricola [ncbi taxid: 265085]
  68. Prorocentrum micans [ncbi taxid: 2945]
  69. Pteris semipinnata [ncbi taxid: 265705]
  70. Pterocaulon serrulatum [ncbi taxid: 1548653]
  71. Pulsatilla chinensis [ncbi taxid: 714493]
  72. Punica granatum [ncbi taxid: 22663]
  73. Quercus marilandica [ncbi taxid: 478951]
  74. Rapanea lancifolia [ncbi taxid: ]
  75. Rosaceae [ncbi taxid: 3745]
  76. Rubia akane [ncbi taxid: ]
  77. Salix rosmarinifolia [ncbi taxid: 2720589]
  78. Salvia hispanica [ncbi taxid: 49212]
  79. Salvia lavanduloides [ncbi taxid: 392669]
  80. Salvia patens [ncbi taxid: 392677]
  81. Salvia virgata [ncbi taxid: 1298553]
  82. Scorzonera pseudodivaricata [ncbi taxid: ]
  83. Senecio platyphylloides [ncbi taxid: ]
  84. Spatholobus suberectus [ncbi taxid: 455371]
  85. Sphaeria rousseliana [ncbi taxid: ]
  86. Syncarpia hillii [ncbi taxid: 271921]
  87. Thalassiosira weissflogii [ncbi taxid: ]
  88. Xenoacremonium recifei [ncbi taxid: 1036759]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-7897 flavonoid di-C-glucosylation
BioCyc:META_PWY-6515 phloridzin biosynthesis
PlantCyc:SPIRODELA_PWY-6515 phloridzin biosynthesis
PlantCyc:SVIRIDIS_PWY-6515 phloridzin biosynthesis
PlantCyc:AMBORELLA_PWY-6515 phloridzin biosynthesis
PlantCyc:PPERSICA_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:RCHINENSIS_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:RUBBERTREE_PWY-6515 phloridzin biosynthesis
PlantCyc:RUBBERTREE_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:SORGHUMBICOLOR_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:SOY_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:SPENNELLII_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:SUGARBEET_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:SWEETCHERRY_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:CORN_PWY-6515 phloridzin biosynthesis
PlantCyc:TOMATO_PWY-7897 flavonoid di-C-glucosylation
PlantCyc:VALLEYOAK_PWY-6515 phloridzin biosynthesis
PlantCyc:OMERIDIONALIS_PWY-6515 phloridzin biosynthesis
PlantCyc:FVESCA_VESCA_PWY-6515 phloridzin biosynthesis
PlantCyc:ORYZA_PWY-7897 flavonoid di-C-glucosylation
View All Pathways