Apigenin 7,4'-dimethyl ether (BioCAD00000006696)

plant natural products microbial natural products

Metabolite Card

Formula: C17H14O5 (298.0841)
SMILES: COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C=C(OC)C=C2O1

Synonyms [en]

Apigenin 7,4'-dimethyl ether; Genkwanin 4'-methyl ether; apigenin dimethylether; 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one; 5-hydroxy-4',7-dimethoxyflavone; 4',7-Dimethylapigenin

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Apigenin 7,4'-dimethyl ether. 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: BioCAD00000006696). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Apigenin 7,4'-dimethyl ether, also known as apigenin dimethylether or 4',7-dimethylapigenin, belongs to the class of organic compounds known as 7-O-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, apigenin 7,4'-dimethyl ether is considered to be a flavonoid lipid molecule. Apigenin 7,4'-dimethyl ether is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, apigenin 7,4'-dimethyl ether has been detected, but not quantified in, common sages and sweet basils. This could make apigenin 7,4'-dimethyl ether a potential biomarker for the consumption of these foods. BioTransformer predicts that apigenin 7,4'-dimethyl ether is a product of 4',5,7-trimethoxyflavone metabolism via an O-dealkylation reaction and catalyzed by CYP2C9 and CYP2C19 enzymes (PMID: 30612223).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 137988-02-4
  • CAS Registry Number: 137988-03-5
  • CAS Registry Number: 29219-05-4
  • CAS Registry Number: 33513-36-9
  • CAS Registry Number: 36768-27-1
  • CAS Registry Number: 5128-44-9
  • CAS Registry Number: 63046-10-6
  • CAS Registry Number: 80710-38-9
  • CAS Registry Number: 88126-44-7
  • CAS Registry Number: 94451-48-6
  • PubChem: 5281601
  • ChEBI: ChEBI:2769
  • HMDB: HMDB0132454
  • LipidMaps: LMPK12111029
  • KEGG: C10019
  • BioCyc: CPD-15631
  • NCBI MeSH: apigenin dimethylether
  • RefMet: RM0186709
  • MoNA: VF-NPL-LTQ007259
  • MoNA: VF-NPL-LTQ007260
  • MoNA: VF-NPL-LTQ007261
  • MoNA: VF-NPL-LTQ007262
  • MoNA: VF-NPL-QEHF014461
  • MoNA: VF-NPL-QEHF014462
  • MoNA: VF-NPL-QEHF014463
  • MoNA: VF-NPL-QEHF014464
  • MoNA: VF-NPL-QEHF014465
  • MoNA: VF-NPL-QEHF014466
  • MoNA: VF-NPL-QTOF006703
  • MoNA: VF-NPL-QTOF006704
  • MoNA: VF-NPL-QTOF006705
  • Metlin: METLIN_49456
  • Coconut NaturalProduct: CNP0025104.0
  • Coconut NaturalProduct: CNP0056776.0
  • Coconut NaturalProduct: CNP0114476.0
  • Coconut NaturalProduct: CNP0118071.0
  • Coconut NaturalProduct: CNP0156106.0
  • Coconut NaturalProduct: CNP0156699.0
  • Coconut NaturalProduct: CNP0178015.0
  • Coconut NaturalProduct: CNP0226960.0
  • Coconut NaturalProduct: CNP0242739.0
  • Coconut NaturalProduct: CNP0244105.0
  • Coconut NaturalProduct: CNP0245380.0
  • Coconut NaturalProduct: CNP0272364.0
  • Coconut NaturalProduct: CNP0282504.0
  • Coconut NaturalProduct: CNP0299894.0
  • Coconut NaturalProduct: CNP0311798.0
  • Coconut NaturalProduct: CNP0393445.0
  • Coconut NaturalProduct: CNP0396936.0
  • Coconut NaturalProduct: CNP0486470.0
  • Coconut NaturalProduct: CNP0534286.0
  • Coconut NaturalProduct: CNP0567705.0

Class / Ontology

Metabolic Network
ID EC Number Name
Rhea:RHEA:73108 acacetin + S-adenosyl-L-methionine => apigenin 4',7-dimethyl ether + S-adenosyl-L-homocysteine
Rhea:RHEA:73109 apigenin 4',7-dimethyl ether + S-adenosyl-L-homocysteine => acacetin + S-adenosyl-L-methionine
Rhea:RHEA:73110 acacetin + S-adenosyl-L-methionine <=> apigenin 4',7-dimethyl ether + S-adenosyl-L-homocysteine
Rhea:RHEA:73264 genkwanin + S-adenosyl-L-methionine => apigenin 4',7-dimethyl ether + S-adenosyl-L-homocysteine
Rhea:RHEA:73265 apigenin 4',7-dimethyl ether + S-adenosyl-L-homocysteine => genkwanin + S-adenosyl-L-methionine
Rhea:RHEA:73266 genkwanin + S-adenosyl-L-methionine <=> apigenin 4',7-dimethyl ether + S-adenosyl-L-homocysteine
Rhea:RHEA:73436 apigenin 4',7-dimethyl ether + reduced [NADPH—hemoprotein reductase] + O2 => ladanein + oxidized [NADPH—hemoprotein reductase] + H2O + H+
Rhea:RHEA:73437 ladanein + oxidized [NADPH—hemoprotein reductase] + H2O + H+ => apigenin 4',7-dimethyl ether + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:73438 apigenin 4',7-dimethyl ether + reduced [NADPH—hemoprotein reductase] + O2 <=> ladanein + oxidized [NADPH—hemoprotein reductase] + H2O + H+
BioCyc:RXN-14750 2.1.1.- S-ADENOSYLMETHIONINE + CPD-15486 --> PROTON + CPD-15631 + ADENOSYL-HOMO-CYS
BioCyc:RXN-14751 1.14.14.- CPD-15631 + OXYGEN-MOLECULE + Red-NADPH-Hemoprotein-Reductases --> CPD-15632 + WATER + Ox-NADPH-Hemoprotein-Reductases
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Organism Source

Taxonomy Source

  1. Coutarea hexandra [ncbi taxid: 85718]
  2. Aconitum variegatum [ncbi taxid: 112594]
  3. Cheilanthes fragrans [ncbi taxid: ]
  4. Fadogia agrestis [ncbi taxid: ]
  5. Kaempferia parviflora [ncbi taxid: 97751]
  6. Murraya paniculata [ncbi taxid: 43711]
  7. Ostrya carpinifolia [ncbi taxid: 176865]
  8. Stephania dielsiana [ncbi taxid: 1501458]
  9. Pycnanthus angolensis [ncbi taxid: 224864]
  10. Virola surinamensis [ncbi taxid: 224910]
  11. Launaea asplenifolia [ncbi taxid: ]
  12. Henriettella fascicularis [ncbi taxid: ]
  13. Callistemon acuminatus [ncbi taxid: 73723]
  14. Callistemon juniperinus [ncbi taxid: ]
  15. Callistemon lanceolatus [ncbi taxid: 155884]
  16. Callistemon rigidus [ncbi taxid: 73733]
  17. Callistemon salignus [ncbi taxid: 73735]
  18. Callistemon salignus var.viridiflorus [ncbi taxid: ]
  19. Callistemon speciosus [ncbi taxid: ]
  20. Callistemon spp. [ncbi taxid: ]
  21. Pancratium maritimum [ncbi taxid: 644807]
  22. Syzygium alternifolium [ncbi taxid: ]
  23. Acacia aneura [ncbi taxid: 205021]
  24. Acacia ixiophylla [ncbi taxid: 1120458]
  25. Acamptopappus shockleyi [ncbi taxid: 217566]
  26. Aconitum variegatum [ncbi taxid: 112594]
  27. Aegialitis annulata [ncbi taxid: 124972]
  28. Afrocarpus gracilior [ncbi taxid: 165205]
  29. Agave xylonacantha [ncbi taxid: 3450508]
  30. Alnus japonica [ncbi taxid: 109063]
  31. Aloe speciosa [ncbi taxid: 1080012]
  32. Alpinia oxyphylla [ncbi taxid: 125261]
  33. Amaracus pampanini [ncbi taxid: ]
  34. Amorphophallus konjac [ncbi taxid: 78372]
  35. Anarrhinum forskahlii [ncbi taxid: ]
  36. Andrographis paniculata [ncbi taxid: 175694]
  37. Angelica saxatilis [ncbi taxid: 357965]
  38. Aniba riparia [ncbi taxid: ]
  39. Aniba santalodora [ncbi taxid: ]
  40. Anthemis cretica [ncbi taxid: 127978]
  41. Antiphiona pinnatisecta [ncbi taxid: 81504]
  42. Antirrhinum spp. [ncbi taxid: ]
  43. Artabotrys uncinatus [ncbi taxid: ]
  44. Artemisia afra [ncbi taxid: 72333]
  45. Artemisia diffusa [ncbi taxid: 1287603]
  46. Astragalus circassicus [ncbi taxid: ]
  47. Baccharis crispa [ncbi taxid: ]
  48. Baccharis rhomboidalis [ncbi taxid: 3027732]
  49. Baccharis trinervis [ncbi taxid: 573714]
  50. Beilschmiedia madang [ncbi taxid: ]
  51. Bethencourtia palmensis [ncbi taxid: 462391]
  52. Betula nigra [ncbi taxid: 3508]
  53. Beyeria [ncbi taxid: 316914]
  54. Boesenbergia pandurata [ncbi taxid: ]
  55. Bonellia macrocarpa [ncbi taxid: 232881]
  56. Boswellia ovalifoliolata [ncbi taxid: 613108]
  57. Breonia chinensis [ncbi taxid: 170042]
  58. Calea ternifolia [ncbi taxid: 1475378]
  59. Callicarpa americana [ncbi taxid: 204211]
  60. Calophyllum inophyllum [ncbi taxid: 158927]
  61. Campanula choziatowskyi [ncbi taxid: ]
  62. Campylotropis hirtella [ncbi taxid: 1108177]
  63. Centaurea scoparia [ncbi taxid: 2072395]
  64. Centaurea sonchifolia [ncbi taxid: ]
  65. Ceropegia dichotoma [ncbi taxid: 424975]
  66. Cheilanthes fragrans [ncbi taxid: ]
  67. Cheilanthes grisea [ncbi taxid: 243791]
  68. Chrysanthemum indicum [ncbi taxid: 146995]
  69. Cistus clusii [ncbi taxid: 335182]
  70. Cistus spp. [ncbi taxid: ]
  71. Colchicum filifolium [ncbi taxid: 280460]
  72. Crinum moorei [ncbi taxid: 82223]
  73. Crotalaria candicans [ncbi taxid: ]
  74. Cunila angustifolia [ncbi taxid: ]
  75. Currania robertiana [ncbi taxid: ]
  76. Cynoglossum macrostylum [ncbi taxid: 1452877]
  77. Daedaleopsis tricolor [ncbi taxid: 76330]
  78. Daphne genkwa [ncbi taxid: 1477590]
  79. Dendrobium loddigesii [ncbi taxid: 117954]
  80. Derris indica [ncbi taxid: ]
  81. Dialium excelsum [ncbi taxid: 1608024]
  82. Distephanus angulifolius [ncbi taxid: 3123265]
  83. Dodonaea viscosa [ncbi taxid: 151065]
  84. Dorystoechas hastata [ncbi taxid: ]
  85. Drymaria cordata [ncbi taxid: 191453]
  86. Dysidea fragilis [ncbi taxid: 1336851]
  87. Ekebergia capensis [ncbi taxid: 124949]
  88. Enicosanthum cupulare [ncbi taxid: ]
  89. Eremophila homoplastica [ncbi taxid: 2652550]
  90. Eria japonica [ncbi taxid: ]
  91. Erythrina hypaphorus [ncbi taxid: ]
  92. Escallonia pulverulenta [ncbi taxid: 178796]
  93. Esox lucius [ncbi taxid: 8010]
  94. Etmopterus spinax [ncbi taxid: 648166]
  95. Eucalyptus apodophylla [ncbi taxid: 1711146]
  96. Eucalyptus globulus subsp. bicostata [ncbi taxid: 71272]
  97. Eucalyptus torelliana [ncbi taxid: ]
  98. Eucryphia [ncbi taxid: 3790]
  99. Eucryphia spp. [ncbi taxid: ]
  100. Eugenia formosa [ncbi taxid: ]
  101. Euphorbia hylonoma [ncbi taxid: 526195]
  102. Euphorbia latazi [ncbi taxid: ]
  103. Fadogia agrestis [ncbi taxid: ]
  104. Flavobacterium johnsoniae [ncbi taxid: 986]
  105. Garcinia gaudichaudii [ncbi taxid: 2516490]
  106. Geigeria filifolia [ncbi taxid: ]
  107. Gentiana makinoi [ncbi taxid: 2163617]
  108. Glycosmis macrophylla [ncbi taxid: 1489662]
  109. Gypsophila perfoliata [ncbi taxid: 515457]
  110. Hardenbergia violacea [ncbi taxid: 53885]
  111. Helicoverpa armigera [ncbi taxid: 29058]
  112. Heliotropium scabrum [ncbi taxid: ]
  113. Helleborus macranthus [ncbi taxid: ]
  114. Hieracium amplexicaule [ncbi taxid: 269348]
  115. Hypericum elodes [ncbi taxid: 673926]
  116. Hypericum polyanthemum [ncbi taxid: 1341051]
  117. Hyptis albida [ncbi taxid: ]
  118. Ilex goshiensis [ncbi taxid: 53203]
  119. Iris kashmiriana [ncbi taxid: ]
  120. Isodon flavidus [ncbi taxid: 662909]
  121. Juniperus drupacea [ncbi taxid: 103973]
  122. Kaempferia parviflora [ncbi taxid: 97751]
  123. Lactarius mitissimus [ncbi taxid: 118866]
  124. Laurencia decumbens [ncbi taxid: 997938]
  125. Lemonia spectabilis [ncbi taxid: ]
  126. Lepechinia urbanii [ncbi taxid: 1405049]
  127. Letharia vulpina [ncbi taxid: 129387]
  128. Leucas cephalotes SPRENG. [ncbi taxid: ]
  129. Leuconostoc mesenteroides [ncbi taxid: 1245]
  130. Litsea monopetala [ncbi taxid: 344080]
  131. Lonchocarpus chiricanus [ncbi taxid: 1582177]
  132. Lycopodium japonicum [ncbi taxid: 672196]
  133. Lycopus virginicus [ncbi taxid: 1620142]
  134. Maackia tashiroi [ncbi taxid: 256641]
  135. Maclura cochinchinensis [ncbi taxid: 194324]
  136. Marchesinia brachiata [ncbi taxid: 264480]
  137. Martensia denticulata [ncbi taxid: 1364885]
  138. Matricaria sabulosa [ncbi taxid: ]
  139. Matsucoccus josephi [ncbi taxid: ]
  140. Mentha cardiaca [ncbi taxid: ]
  141. Mentzelia decapetala [ncbi taxid: 37834]
  142. Metanarthecium luteoviride [ncbi taxid: 1112727]
  143. Millettia usaramensis [ncbi taxid: 1258704]
  144. Mimosa pigra [ncbi taxid: 367322]
  145. Mirabilis viscosa [ncbi taxid: 1424733]
  146. Monoclea gottschei [ncbi taxid: 56937]
  147. Mucuna holtonii [ncbi taxid: 1127093]
  148. Nepytia freemani [ncbi taxid: 942327]
  149. Nuxia sphaerocephala [ncbi taxid: ]
  150. Ocimum americanum L.var.pilosum (Willd.) Paton [ncbi taxid: ]
  151. Ocimum basilicum L. [ncbi taxid: ]
  152. Ocimum minimum L. [ncbi taxid: ]
  153. Ocimum x citriodorum Vis. [ncbi taxid: ]
  154. Ononis spinosa [ncbi taxid: 58890]
  155. Ophyrosporus charrua [ncbi taxid: ]
  156. Orgyia pseudotsugata [ncbi taxid: 33414]
  157. Oroxylum indicum [ncbi taxid: 83951]
  158. Ostrya carpinifolia [ncbi taxid: 176865]
  159. Pandanus tectorius [ncbi taxid: 4726]
  160. Parmotrema nilgherrense [ncbi taxid: 1450753]
  161. Passiflora foetida [ncbi taxid: 159421]
  162. Pentaclethra macrophylla [ncbi taxid: 148716]
  163. Peperomia dindygulensis [ncbi taxid: 1972104]
  164. Peperomia dindygulensis Miq. [ncbi taxid: ]
  165. Peperomia sui [ncbi taxid: ]
  166. Periploca sepium [ncbi taxid: 190712]
  167. Perovskia spp. [ncbi taxid: ]
  168. Petunia axillaris subsp. parodii [ncbi taxid: 55890]
  169. Piper peepuloides [ncbi taxid: 1595994]
  170. Plectranthus myrianthus [ncbi taxid: ]
  171. Podocarpus dacrydioides [ncbi taxid: ]
  172. Polytrichastrum alpinum [ncbi taxid: 129212]
  173. Preussia terricola [ncbi taxid: 265085]
  174. Pseudocyclosorus subochthodes [ncbi taxid: 1132564]
  175. Pterocaulon serrulatum [ncbi taxid: 1548653]
  176. Pterocaulon virgatum [ncbi taxid: 1257061]
  177. Pulsatilla chinensis [ncbi taxid: 714493]
  178. Quercus marilandica [ncbi taxid: 478951]
  179. Rhodiola semenovii [ncbi taxid: 666566]
  180. Rhus undulata [ncbi taxid: ]
  181. Roseivirga echinicomitans [ncbi taxid: 296218]
  182. Rosmarinus officinalis [ncbi taxid: ]
  183. Rubia akane [ncbi taxid: ]
  184. Salix rosmarinifolia [ncbi taxid: 2720589]
  185. Salvia dorrii [ncbi taxid: 207754]
  186. Salvia hypoleuca [ncbi taxid: 1294397]
  187. Salvia lavandulifolia [ncbi taxid: ]
  188. Salvia lavanduloides [ncbi taxid: 392669]
  189. Salvia macrosiphon [ncbi taxid: 1571166]
  190. Salvia moorcroftiana [ncbi taxid: 1585254]
  191. Salvia nicolsoniana [ncbi taxid: ]
  192. Salvia officinalis [ncbi taxid: 38868]
  193. Salvia palaestina [ncbi taxid: 268920]
  194. Salvia patens [ncbi taxid: 392677]
  195. Salvia sapinae [ncbi taxid: ]
  196. Salvia sclarea [ncbi taxid: 38869]
  197. Salvia sessei [ncbi taxid: 933147]
  198. Salvia spp. [ncbi taxid: ]
  199. Salvia syriaca [ncbi taxid: 1685717]
  200. Salvia texana [ncbi taxid: 268932]
  201. Salvia verbenaca [ncbi taxid: 268912]
  202. Salvia virgata [ncbi taxid: 1298553]
  203. Salvia yosgadensis [ncbi taxid: 1933769]
  204. Sarcococca saligna [ncbi taxid: 153583]
  205. Schizonella melanogramma [ncbi taxid: 63386]
  206. Scutellaria barbata [ncbi taxid: 396367]
  207. Senecio platyphylloides [ncbi taxid: ]
  208. Sideritis spp. [ncbi taxid: ]
  209. Sonneratia caseolaris [ncbi taxid: 122814]
  210. Sphaeria rousseliana [ncbi taxid: ]
  211. Stephania dielsiana [ncbi taxid: 1501458]
  212. Stephania zippeliana [ncbi taxid: ]
  213. Streblognathus aethiopicus [ncbi taxid: 373804]
  214. Streptomyces avermitilis (SaOMT2) [ncbi taxid: ]
  215. Streptomyces bobili [ncbi taxid: 67280]
  216. Streptomyces psammoticus SCSIO NS126 [ncbi taxid: ]
  217. Striga asiatica [ncbi taxid: 4170]
  218. Talaromyces variabilis [ncbi taxid: 28576]
  219. Teucrium marum [ncbi taxid: 711380]
  220. Teucrium polium [ncbi taxid: 1117157]
  221. Teucrium ramosissimum [ncbi taxid: ]
  222. Thalassiosira weissflogii [ncbi taxid: ]
  223. Thymus piperella [ncbi taxid: ]
  224. Tristania conferta [ncbi taxid: ]
  225. Trocholejeunea scandvicensis [ncbi taxid: ]
  226. Tubularia larynx [ncbi taxid: ]
  227. Turnera diffusa [ncbi taxid: 329212]
  228. Vernonia cistifolia [ncbi taxid: ]
  229. Veronica polita [ncbi taxid: 195136]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-7325 salvigenin biosynthesis
BioCyc:ARA_PWY-7325 salvigenin biosynthesis
PlantCyc:SOY_PWY-7325 salvigenin biosynthesis
PlantCyc:SPENNELLII_PWY-7325 salvigenin biosynthesis
PlantCyc:AHALLERI_PWY-7325 salvigenin biosynthesis
PlantCyc:ALYRATA_PWY-7325 salvigenin biosynthesis
PlantCyc:TOMATO_PWY-7325 salvigenin biosynthesis
PlantCyc:TPARVULA_PWY-7325 salvigenin biosynthesis
PlantCyc:CCAPSULARIS_PWY-7325 salvigenin biosynthesis
PlantCyc:CGIGANTEA_PWY-7325 salvigenin biosynthesis
PlantCyc:CLEMENTINE_PWY-7325 salvigenin biosynthesis
PlantCyc:CROSEUS_PWY-7325 salvigenin biosynthesis
PlantCyc:VALLEYOAK_PWY-7325 salvigenin biosynthesis
PlantCyc:HOP_PWY-7325 salvigenin biosynthesis
PlantCyc:DATEPALM_PWY-7325 salvigenin biosynthesis
PlantCyc:LER_PWY-7325 salvigenin biosynthesis
PlantCyc:WATERMELON_PWY-7325 salvigenin biosynthesis
PlantCyc:PINEAPPLE_PWY-7325 salvigenin biosynthesis
PlantCyc:SWEETORANGE_PWY-7325 salvigenin biosynthesis
PlantCyc:ARA_PWY-7325 salvigenin biosynthesis
View All Pathways