Naringenin chalcone (BioCAD00000015039)

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Metabolite Card

Formula: C15H12O5 (272.0685)
SMILES: OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2O)C=C1

Synonyms [en]

Naringenin chalcone; Chalconaringenin; Isosalipurpol; 2',4,4',6'-tetrahydroxychalcone; 2'4'6'4-Tetrahydroxychalcone; 2',4',6',4-Tetrahydroxychalcone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Naringenin chalcone. 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: BioCAD00000015039). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Chalconaringenin is found in garden tomato. Chalconaringenin is isolated from tomato fruit cuticle

Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 25515-46-2
  • CAS Registry Number: 5071-40-9
  • CAS Registry Number: 73692-50-9
  • PubChem: 5280960
  • ChEBI: ChEBI:15413
  • HMDB: HMDB0029631
  • LipidMaps: LMPK12120264
  • KEGG: C06561
  • BioCyc: CPD-20012
  • NCBI MeSH: naringenin chalcone
  • Wikipedia: Naringenin chalcone
  • Wikipedia: Naringenin_chalcone
  • RefMet: RM0204665
  • MoNA: PB000126
  • MoNA: PB000127
  • MoNA: PB000128
  • MoNA: PB000129
  • MoNA: PB002405
  • MoNA: PB002406
  • MoNA: PB002407
  • MoNA: PB002408
  • MoNA: Polyphenol000439
  • Metlin: METLIN_3402
  • Coconut NaturalProduct: CNP0305890.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R01613 2.3.1.74 malonyl-CoA:4-coumaroyl-CoA malonyltransferase(cyclizing)
KEGG:R02446 5.5.1.6 flavanone lyase (decyclizing)
KEGG:R07224 1.21.3.6 2',4,4',6'-tetrahydroxychalcone:oxygen oxidoreductase
KEGG:R08003 C06561 + C00235<=>C16416 + C00013
KEGG:R08006 2.4.1.286 UDP-alpha-D-glucose:2',4,4',6'-tetrahydroxychalcone 4'-O-beta-D-glucosyltransferase
KEGG:R08013 2.4.1.- C06561 + C00029<=>C16406 + C00015
Rhea:RHEA:11129 2.3.1.156 (E)-4-coumaroyl-CoA + 3 malonyl-CoA + 3 H+ => 2',4,4',6'-tetrahydroxychalcone + 3 CO2 + 4 CoA
Rhea:RHEA:11130 2.3.1.156 2',4,4',6'-tetrahydroxychalcone + 3 CO2 + 4 CoA => (E)-4-coumaroyl-CoA + 3 malonyl-CoA + 3 H+
Rhea:RHEA:11131 2.3.1.156 (E)-4-coumaroyl-CoA + 3 malonyl-CoA + 3 H+ <=> 2',4,4',6'-tetrahydroxychalcone + 3 CO2 + 4 CoA
Rhea:RHEA:34292 2.4.1.286 2',4,4',6'-tetrahydroxychalcone + UDP-α-D-glucose => 2',4,4',6'-tetrahydroxychalcone 4'-O-β-D-glucoside + UDP + H+
Rhea:RHEA:34293 2.4.1.286 2',4,4',6'-tetrahydroxychalcone 4'-O-β-D-glucoside + UDP + H+ => 2',4,4',6'-tetrahydroxychalcone + UDP-α-D-glucose
Rhea:RHEA:34294 2.4.1.286 2',4,4',6'-tetrahydroxychalcone + UDP-α-D-glucose <=> 2',4,4',6'-tetrahydroxychalcone 4'-O-β-D-glucoside + UDP + H+
Rhea:RHEA:51877 2.5.1.136 2',4,4',6'-tetrahydroxychalcone + dimethylallyl diphosphate => desmethylxanthohumol + diphosphate
Rhea:RHEA:51878 2.5.1.136 desmethylxanthohumol + diphosphate => 2',4,4',6'-tetrahydroxychalcone + dimethylallyl diphosphate
Rhea:RHEA:51879 2.5.1.136 2',4,4',6'-tetrahydroxychalcone + dimethylallyl diphosphate <=> desmethylxanthohumol + diphosphate
Rhea:RHEA:79892 5.5.1.6 2',4,4',6'-tetrahydroxychalcone => (2S)-naringenin
Rhea:RHEA:79893 5.5.1.6 (2S)-naringenin => 2',4,4',6'-tetrahydroxychalcone
Rhea:RHEA:79894 5.5.1.6 2',4,4',6'-tetrahydroxychalcone <=> (2S)-naringenin
BioCyc:RXN-8283 2.4.1.- CPD-12575 + CPD-20012 --> PROTON + CPD-8062 + UDP
BioCyc:RXN-7820 2.5.1.136 CPD-20012 + CPD-4211 --> PROTON + CPD-7120 + PPI
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Organism Source

Taxonomy Source

  1. Absidia repens [ncbi taxid: 90262]
  2. Abuta panurensis [ncbi taxid: ]
  3. Adoxophyes orana [ncbi taxid: 480707]
  4. Allium aflatunense [ncbi taxid: 70752]
  5. Allium minutiflorum [ncbi taxid: 543691]
  6. Alpinia rafflesiana [ncbi taxid: 105680]
  7. Ambrosia artemisioides [ncbi taxid: 2067507]
  8. Arabidopsis thaliana [ncbi taxid: 3702]
  9. Aristeomorpha foliacea [ncbi taxid: ]
  10. Birgus latro [ncbi taxid: 177283]
  11. Bostrychia scorpioides [ncbi taxid: 324764]
  12. Calea clematidea [ncbi taxid: 3464887]
  13. Cassia absus [ncbi taxid: ]
  14. Casuarina glauca [ncbi taxid: 3522]
  15. Chamaecrista absus [ncbi taxid: 592576]
  16. Chrysolina hyperici [ncbi taxid: 111402]
  17. Citrullus lanatus [ncbi taxid: 3654]
  18. Curvularia falcata [ncbi taxid: 2074906]
  19. Cydonia vulgaris [ncbi taxid: ]
  20. Dalbergia inundata [ncbi taxid: 1353457]
  21. Dalbergia retusa [ncbi taxid: 466221]
  22. Dianthus sp. [ncbi taxid: 137602]
  23. Discoglossus pictus [ncbi taxid: 8351]
  24. Dolomedes okefinokensis [ncbi taxid: 2835808]
  25. Duboisia leichhardtii [ncbi taxid: 195736]
  26. Elaeocarpus ganitrus [ncbi taxid: 2508994]
  27. Ephedra frustillata [ncbi taxid: 173277]
  28. Eucalyptus consideniana [ncbi taxid: 713921]
  29. Eucalyptus grossa [ncbi taxid: 1711331]
  30. Euphorbia laurifolia [ncbi taxid: 212926]
  31. Euryspongia arenaria [ncbi taxid: ]
  32. Haemanthus puniceus [ncbi taxid: ]
  33. Helichrysum sp. [ncbi taxid: 3128019]
  34. Heywoodiella oligocephala [ncbi taxid: ]
  35. Humulus lupulus [ncbi taxid: 3486]
  36. Hydrocotyle vulgaris [ncbi taxid: 82091]
  37. Hypericum patulum [ncbi taxid: 212239]
  38. Ipomoea nil [ncbi taxid: 35883]
  39. Lepraria lobificans [ncbi taxid: 209135]
  40. Libanotis condensata [ncbi taxid: 1917944]
  41. Lobelia cardinalis [ncbi taxid: 76578]
  42. Lonicera racemosa [ncbi taxid: ]
  43. Lycopersicon esculentum [ncbi taxid: ]
  44. Mallotus metcalfianus [ncbi taxid: 463330]
  45. Meum athamanticum [ncbi taxid: 82093]
  46. Mucuna membranacea [ncbi taxid: ]
  47. Nepeta argolica [ncbi taxid: 3057216]
  48. Nothofagus antarctica [ncbi taxid: 28933]
  49. Orchis fusca [ncbi taxid: ]
  50. Oxalis repens [ncbi taxid: ]
  51. Paeonia sp. [ncbi taxid: 3073249]
  52. Petunia hybrid [ncbi taxid: ]
  53. Petunia x hybrida [ncbi taxid: 4102]
  54. Polianthes tuberosa [ncbi taxid: ]
  55. Populus angustifolia [ncbi taxid: 351344]
  56. Populus sieboldii [ncbi taxid: ]
  57. Psorospermum molluscum [ncbi taxid: ]
  58. Pterocarpus indica [ncbi taxid: ]
  59. Salix purpurea [ncbi taxid: 77065]
  60. Senecio algens [ncbi taxid: 462498]
  61. Senecio anteuphorbium [ncbi taxid: 405104]
  62. Sinularia granosa [ncbi taxid: ]
  63. Solanum habrochaites [ncbi taxid: 62890]
  64. Spatholobus suberectus [ncbi taxid: 455371]
  65. Sphyraena japonica [ncbi taxid: 392545]
  66. Stevia yaconensis [ncbi taxid: ]
  67. Streptomyces venezuelae [ncbi taxid: 54571]
  68. Tephrosia virginiana [ncbi taxid: 1089629]
  69. Tulipa sp. [ncbi taxid: ]
  70. Virola calophylloidea [ncbi taxid: ]
  71. Vitis cinerea [ncbi taxid: 226012]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-1901 aurone biosynthesis
BioCyc:META_PWY1F-FLAVSYN flavonoid biosynthesis
BioCyc:META_PWY-7897 flavonoid di-C-glucosylation
BioCyc:META_PWY-7397 naringenin biosynthesis (engineered)
BioCyc:ARA_PWY-6787 flavonoid biosynthesis (in equisetum)
BioCyc:META_PWY-5339 chalcone 2'-O-glucoside biosynthesis
BioCyc:ARA_PWY1F-FLAVSYN flavonoid biosynthesis
BioCyc:META_PWY-5135 xanthohumol biosynthesis
BioCyc:META_PWY-6787 flavonoid biosynthesis (in equisetum)
BioCyc:META_PWY-6316 aromatic polyketides biosynthesis
PlantCyc:SOY_PWY-6787 flavonoid biosynthesis (in equisetum)
PlantCyc:SPIRODELA_PWY-6787 flavonoid biosynthesis (in equisetum)
PlantCyc:SUGARBEET_PWY1F-FLAVSYN flavonoid biosynthesis
PlantCyc:AHALLERI_PWY1F-FLAVSYN flavonoid biosynthesis
PlantCyc:SWEETORANGE_PWY-6787 flavonoid biosynthesis (in equisetum)
PlantCyc:SWEETORANGE_PWY1F-FLAVSYN flavonoid biosynthesis
PlantCyc:TPARVULA_PWY1F-FLAVSYN flavonoid biosynthesis
PlantCyc:ARA_PWY-6787 flavonoid biosynthesis (in equisetum)
PlantCyc:ASPARAGUS_PWY-6787 flavonoid biosynthesis (in equisetum)
PlantCyc:WHEATA_PWY-6787 flavonoid biosynthesis (in equisetum)
View All Pathways