Naringenin 7-O-beta-D-glucoside (BioCAD00000015038)

plant natural products microbial natural products

Metabolite Card

Formula: C21H22O10 (434.1213)
SMILES: C1(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)C=C2O[C@]([H])(C3C=CC(O)=CC=3)CC(=O)C2=C(O)C=1

Synonyms [en]

Prunin; Naringenin 7-O-beta-D-glucoside; (2S)-naringenin 7-O-beta-D-glucoside; Naringenin-7-O-glucoside; LSB8HDX4E5; 1ST175404

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Naringenin 7-O-beta-D-glucoside. 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: BioCAD00000015038). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Prunin

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 23711-00-4
  • CAS Registry Number: 529-55-5
  • PubChem: 92794
  • ChEBI: ChEBI:28327
  • LipidMaps: LMPK12140237
  • KEGG: C09099
  • BioCyc: NARINGENIN-7-O-BETA-D-GLUCOSIDE
  • Wikipedia: Prunin
  • RefMet: RM0157110
  • MoNA: MoNA_0001725
  • MoNA: MoNA_0001726
  • MoNA: MoNA_0001727
  • MoNA: MoNA_0001728
  • MoNA: MoNA_0001729
  • MoNA: MoNA_0001730
  • MoNA: PM000414
  • MoNA: PR020069
  • MoNA: PR040149
  • MoNA: PR040150
  • MoNA: PR040151
  • MoNA: PR040152
  • MoNA: PR040153
  • MoNA: PR040154
  • MoNA: PR040155
  • MoNA: PR040156
  • MoNA: PR100249
  • MoNA: PR100671
  • MoNA: PS042801
  • MoNA: PS042802
  • MoNA: PS042803
  • MoNA: PS042804
  • MoNA: PS042805
  • MoNA: PS042806
  • MoNA: PS042807
  • MoNA: PS042808
  • MoNA: PS042809
  • MoNA: PS042810
  • MoNA: PS042811
  • MoNA: TY000160
  • MoNA: TY000161
  • MoNA: TY000162
  • MoNA: VF-NPL-LTQ000204
  • MoNA: VF-NPL-QEHF000439
  • MoNA: VF-NPL-QEHF000440
  • MoNA: VF-NPL-QEHF000441
  • MoNA: VF-NPL-QEHF000442
  • MoNA: VF-NPL-QEHF000443
  • MoNA: VF-NPL-QEHF000444
  • MoNA: VF-NPL-QTOF009412
  • MoNA: VF-NPL-QTOF009413
  • MoNA: VF-NPL-QTOF009414
  • MoNA: VF-NPL-QTOF009415
  • MoNA: VF-NPL-QTOF009416
  • MoNA: VF-NPL-QTOF009417
  • Metlin: METLIN_52725
  • Coconut NaturalProduct: CNP0060415.1
  • Coconut NaturalProduct: CNP0060415.2
  • Coconut NaturalProduct: CNP0060415.3
  • Coconut NaturalProduct: CNP0060415.4
  • Coconut NaturalProduct: CNP0060415.5
  • Coconut NaturalProduct: CNP0060415.6
  • Coconut NaturalProduct: CNP0060415.7
  • Coconut NaturalProduct: CNP0060415.8
  • Coconut NaturalProduct: CNP0228463.1
  • Coconut NaturalProduct: CNP0252815.1
  • Coconut NaturalProduct: CNP0252815.2
  • Coconut NaturalProduct: CNP0269114.1
  • Coconut NaturalProduct: CNP0269114.2
  • Coconut NaturalProduct: CNP0269114.4
  • Coconut NaturalProduct: CNP0269114.5
  • Coconut NaturalProduct: CNP0269114.6
  • Coconut NaturalProduct: CNP0269114.7

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02897 2.4.1.185 UDPglucose:flavanone 7-O-beta-D-glucosyltransferase
KEGG:R06820 2.4.1.236 UDP-L-rhamnose:flavanone-7-O-glucoside 2''-O-alpha-L-rhamnosyltransferase
KEGG:R13064 3.2.1.40 naringin rhamnohydrolase
KEGG:R13081 3.2.1.21 naringenin 7-O-beta-D-glucoside glucohydrolase
Rhea:RHEA:65153 2.4.1.185 (2S)-naringenin + UDP-α-D-glucose => (2S)-naringenin 7-O-β-D-glucoside + UDP + H+
Rhea:RHEA:65154 2.4.1.185 (2S)-naringenin 7-O-β-D-glucoside + UDP + H+ => (2S)-naringenin + UDP-α-D-glucose
Rhea:RHEA:65155 2.4.1.185 (2S)-naringenin + UDP-α-D-glucose <=> (2S)-naringenin 7-O-β-D-glucoside + UDP + H+
Rhea:RHEA:67357 (2S)-naringenin 7-O-β-D-glucoside + malonyl-CoA => (2S)-naringenin 7-O-(6-O-malonyl-β-D-glucoside) + CoA
Rhea:RHEA:67358 (2S)-naringenin 7-O-(6-O-malonyl-β-D-glucoside) + CoA => (2S)-naringenin 7-O-β-D-glucoside + malonyl-CoA
Rhea:RHEA:67359 (2S)-naringenin 7-O-β-D-glucoside + malonyl-CoA <=> (2S)-naringenin 7-O-(6-O-malonyl-β-D-glucoside) + CoA
Rhea:RHEA:69672 (2S)-naringenin 7-O-β-D-glucoside + H2O => (2S)-naringenin + β-D-glucose
Rhea:RHEA:69673 (2S)-naringenin + β-D-glucose => (2S)-naringenin 7-O-β-D-glucoside + H2O
Rhea:RHEA:69674 (2S)-naringenin 7-O-β-D-glucoside + H2O <=> (2S)-naringenin + β-D-glucose
BioCyc:RXN-16248 3.2.1.40 NARINGIN + WATER --> NARINGENIN-7-O-BETA-D-GLUCOSIDE + CPD0-1112
BioCyc:RXN-7732 2.4.1.- UDP-L-RHAMNOSE + NARINGENIN-7-O-BETA-D-GLUCOSIDE --> PROTON + CPD-7059 + UDP
BioCyc:RXN-5381 2.4.1.185 CPD-12575 + NARINGENIN-CMPD --> UDP + NARINGENIN-7-O-BETA-D-GLUCOSIDE + PROTON
BioCyc:RXN-5002 2.4.1.236 UDP-L-RHAMNOSE + NARINGENIN-7-O-BETA-D-GLUCOSIDE --> PROTON + UDP + NARINGIN
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Organism Source

Taxonomy Source

  1. Aplophyllum myrtifolium [ncbi taxid: ]
  2. Cassia obtusifolia [ncbi taxid: ]
  3. Cassia tora [ncbi taxid: ]
  4. Mimusops globosa [ncbi taxid: ]
  5. Wikstroemia monticola [ncbi taxid: ]
  6. Xanthium strumarium var. canadense [ncbi taxid: 552636]
  7. Acacia pycnantha [ncbi taxid: 880440]
  8. Alstonia undulifolia [ncbi taxid: ]
  9. Asteriscus aquaticus [ncbi taxid: 73982]
  10. Betula platyphylla [ncbi taxid: 78630]
  11. Capparis ovata [ncbi taxid: ]
  12. Cassine papillosa [ncbi taxid: ]
  13. Charpentiera obovata [ncbi taxid: 240039]
  14. Cinnamomum subavenium [ncbi taxid: 977953]
  15. Clathria prolifera [ncbi taxid: 1190602]
  16. Conus pulicarius [ncbi taxid: 93154]
  17. Croton montevidensis [ncbi taxid: 323071]
  18. Datisca glomerata [ncbi taxid: 34297]
  19. Dioscorea olfersiana [ncbi taxid: 1933803]
  20. Ecballium elaterium [ncbi taxid: 3679]
  21. Echinus microtuberculatus [ncbi taxid: ]
  22. Fagus fusca [ncbi taxid: ]
  23. Helichrysum auriceps [ncbi taxid: 1442641]
  24. Hubertia tomentosa [ncbi taxid: 462449]
  25. Iotrochota purpurea [ncbi taxid: ]
  26. Ligustrum obtusifolium [ncbi taxid: 178760]
  27. Lotus ucrainicus [ncbi taxid: 1006353]
  28. Metridium senile [ncbi taxid: 6116]
  29. Myelobia smerintha [ncbi taxid: ]
  30. Myristica cagayanensis [ncbi taxid: ]
  31. Ophidiaster ophidianus [ncbi taxid: 232926]
  32. Phebalium dentatum [ncbi taxid: ]
  33. Phyllanthus oligospermus [ncbi taxid: ]
  34. Polygonum flaccidum [ncbi taxid: 2899266]
  35. Prunus persica [ncbi taxid: 3760]
  36. Pseudowintera colorata [ncbi taxid: 22294]
  37. Quercus imbricaria [ncbi taxid: 39469]
  38. Rhodiola crenulata [ncbi taxid: 242839]
  39. Rhodiola kirilowii [ncbi taxid: 203008]
  40. Salix purpurea [ncbi taxid: 77065]
  41. Scrophularia koelzii [ncbi taxid: 1970701]
  42. Solanum andigena [ncbi taxid: ]
  43. Spiracantha cornifolia [ncbi taxid: 1136794]
  44. Streptomyces platensis [ncbi taxid: 58346]
  45. Strychnos nux-vomica [ncbi taxid: 28545]
  46. Tylophora tanakae [ncbi taxid: ]
  47. Vaccinium vitis-idaea [ncbi taxid: 180772]
  48. Viviparus japonicus [ncbi taxid: ]
  49. Acacia adunca [ncbi taxid: 204988]
  50. Acacia farnesiana [ncbi taxid: ]
  51. Adiantum lunulatum [ncbi taxid: ]
  52. Agrostis epigeios [ncbi taxid: ]
  53. Alstonia spathulata [ncbi taxid: ]
  54. Alstonia undulifolia [ncbi taxid: ]
  55. Amathia pinnata [ncbi taxid: ]
  56. Anacystis montana [ncbi taxid: ]
  57. Annona cornifolia [ncbi taxid: 502529]
  58. Annulohypoxylon truncatum [ncbi taxid: 327061]
  59. Artemisia assoana [ncbi taxid: 1227617]
  60. Asteriscus aquaticus [ncbi taxid: 73982]
  61. Asterospicularia laurae [ncbi taxid: 1540332]
  62. Astragalus sempervirens [ncbi taxid: 1532287]
  63. Betula platyphylla [ncbi taxid: 78630]
  64. Bishovia boliviensis [ncbi taxid: ]
  65. Blastochloris viridis [ncbi taxid: 1079]
  66. Calostephane divaricata [ncbi taxid: 1548555]
  67. Capparis ovata [ncbi taxid: ]
  68. Capparis spinosa [ncbi taxid: 65558]
  69. Caragana aurantiaca [ncbi taxid: 626687]
  70. Cassine papillosa [ncbi taxid: ]
  71. Cerbera manghas [ncbi taxid: 141545]
  72. Chaenomeles sinensis [ncbi taxid: ]
  73. Charpentiera obovata [ncbi taxid: 240039]
  74. Cinnamomum subavenium [ncbi taxid: 977953]
  75. Clathria prolifera [ncbi taxid: 1190602]
  76. Clematis tangutica [ncbi taxid: 231661]
  77. Cochlospermum gillivraei [ncbi taxid: 1382064]
  78. Conus pulicarius [ncbi taxid: 93154]
  79. Cotyledon secunda [ncbi taxid: ]
  80. Crotalaria assamica [ncbi taxid: 671522]
  81. Crotalaria pallida [ncbi taxid: 3830]
  82. Croton montevidensis [ncbi taxid: 323071]
  83. Cynara scolymus [ncbi taxid: ]
  84. Datisca glomerata [ncbi taxid: 34297]
  85. Dioscorea olfersiana [ncbi taxid: 1933803]
  86. Dracocephalum tanguticum [ncbi taxid: 1699510]
  87. Drechslera avenae [ncbi taxid: 33199]
  88. Dumortiera hirsuta [ncbi taxid: 56917]
  89. Ecballium elaterium [ncbi taxid: 3679]
  90. Echinus microtuberculatus [ncbi taxid: ]
  91. Eucalyptus melliodora [ncbi taxid: 183838]
  92. Fagus fusca [ncbi taxid: ]
  93. Folium pini [ncbi taxid: ]
  94. Gnetum latifolium [ncbi taxid: 225592]
  95. Goniothalamus malayanus [ncbi taxid: 261094]
  96. Hedysarum connatum [ncbi taxid: ]
  97. Helichrysum auriceps [ncbi taxid: 1442641]
  98. Helipterum roseum [ncbi taxid: ]
  99. Hubertia tomentosa [ncbi taxid: 462449]
  100. Hypericum laricifolium [ncbi taxid: 1136989]
  101. Iotrochota purpurea [ncbi taxid: ]
  102. Ipomoea digitata [ncbi taxid: ]
  103. Ipomoea nil [ncbi taxid: 35883]
  104. Laurencia spectabilis [ncbi taxid: ]
  105. Leathesia nana [ncbi taxid: ]
  106. Lepisorus ussuriensis [ncbi taxid: 699700]
  107. Ligustrum obtusifolium [ncbi taxid: 178760]
  108. Litsea zeylanica [ncbi taxid: ]
  109. Lotus ucrainicus [ncbi taxid: 1006353]
  110. Lycopersicon esculentum [ncbi taxid: ]
  111. Lysimachia mauritiana [ncbi taxid: 306286]
  112. Marrubium anisodon [ncbi taxid: 2291693]
  113. Metridium senile [ncbi taxid: 6116]
  114. Miscanthus sinensis [ncbi taxid: 62337]
  115. Myelobia smerintha [ncbi taxid: ]
  116. Myristica cagayanensis [ncbi taxid: ]
  117. Nasutitermes ephratae [ncbi taxid: 114633]
  118. Naucleopsis ternstroemiiflora [ncbi taxid: 241899]
  119. Oophaga speciosa [ncbi taxid: 43472]
  120. Ophidiaster ophidianus [ncbi taxid: 232926]
  121. Paeonia rockii [ncbi taxid: 62886]
  122. Pastinaca sativa [ncbi taxid: 4041]
  123. Peltostigma guatemalense [ncbi taxid: 1136780]
  124. Phebalium dentatum [ncbi taxid: ]
  125. Phoebe pittieri [ncbi taxid: ]
  126. Phyllanthus emblica [ncbi taxid: ]
  127. Phyllanthus oligospermus [ncbi taxid: ]
  128. Picea vulgaris [ncbi taxid: ]
  129. Polygonum flaccidum [ncbi taxid: 2899266]
  130. Premna odorata [ncbi taxid: 1037421]
  131. Prunus davidiana [ncbi taxid: 151430]
  132. Prunus persica [ncbi taxid: 3760]
  133. Pseudoalteromonas luteoviolacea [ncbi taxid: 43657]
  134. Pseudowintera colorata [ncbi taxid: 22294]
  135. Quercus imbricaria [ncbi taxid: 39469]
  136. Rauvolfia vomitoria [ncbi taxid: 403115]
  137. Rumex maritimus [ncbi taxid: 467604]
  138. Sabina sargentii [ncbi taxid: ]
  139. Salvia syriaca [ncbi taxid: 1685717]
  140. Scrophularia koelzii [ncbi taxid: 1970701]
  141. Scutellaria amoena [ncbi taxid: 1052904]
  142. Silybum marianum [ncbi taxid: 92921]
  143. Sinularia depressa [ncbi taxid: ]
  144. Solanum andigena [ncbi taxid: ]
  145. Solanum laxum [ncbi taxid: 205558]
  146. Spiracantha cornifolia [ncbi taxid: 1136794]
  147. Streptomyces avermectinius [ncbi taxid: ]
  148. Streptomyces platensis [ncbi taxid: 58346]
  149. Swertia franchetiana [ncbi taxid: 50785]
  150. Swertia punctata [ncbi taxid: 1851450]
  151. Theobroma cacao [ncbi taxid: 3641]
  152. Tylophora tanakae [ncbi taxid: ]
  153. Vaccinium oxycoccos [ncbi taxid: 516948]
  154. Viguiera incana [ncbi taxid: 1048928]
  155. Viscum articulatum [ncbi taxid: 50172]
  156. Vitis vinifera [ncbi taxid: 29760]
  157. Viviparus japonicus [ncbi taxid: ]
  158. Wikstroemia retusa [ncbi taxid: 1872696]
  159. Zanthoxylum tetraspermum [ncbi taxid: ]
  160. Citrullus lanatus [ncbi taxid: 3654]
  161. Prunus dulcis [ncbi taxid: 3755]
  162. Solanum lycopersicum [ncbi taxid: 4081]
  163. Agrostis epigeios [ncbi taxid: ]
  164. Annulohypoxylon truncatum [ncbi taxid: 327061]
  165. Clematis tangutica [ncbi taxid: 231661]
  166. Litsea zeylanica [ncbi taxid: ]
  167. Abies spp. [ncbi taxid: ]
  168. Acacia dealbata [ncbi taxid: 205042]
  169. Antirrhinum sp. [ncbi taxid: 29720]
  170. Citrus sudachi [ncbi taxid: 558546]
  171. Coriaria sp. [ncbi taxid: ]
  172. Crotalaria assamica [ncbi taxid: 671522]
  173. Crotalaria pallida [ncbi taxid: 3830]
  174. Dryopteris sp. [ncbi taxid: 3236622]
  175. Lycopersicon esculentum [ncbi taxid: ]
  176. Matthiola sp. [ncbi taxid: ]
  177. Miscanthus sinensis [ncbi taxid: 62337]
  178. Peltophorum pterocarpum [ncbi taxid: 162876]
  179. Phyllanthus emblica [ncbi taxid: ]
  180. Pinus spp. [ncbi taxid: ]
  181. Podocarpus spp. [ncbi taxid: ]
  182. Prunus cerasus [ncbi taxid: 140311]
  183. Prunus persica [ncbi taxid: 3760]
  184. Salix daphnoides [ncbi taxid: 470274]
  185. Salix purpurea [ncbi taxid: 77065]
  186. Theobroma cacao L. [ncbi taxid: ]
  187. Viscum articulactum [ncbi taxid: ]
  188. Viscum coloratum (KOMAR) NAKAI [ncbi taxid: ]
  189. Acacia farnesiana [ncbi taxid: ]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:CROSEUS_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:SWEETORANGE_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:CLEMENTINE_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:COCOA_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:GRAPE_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:PLANT_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:EGRANDIS_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:CACUMINATA_PWY-5094 naringenin glycoside biosynthesis
PlantCyc:GRAIMONDII_PWY-5094 naringenin glycoside biosynthesis
View All Pathways