Liriodenine (BioCAD00000013422)

plant natural products microbial natural products

Metabolite Card

Formula: C17H9NO3 (275.0582)
SMILES: O=C1C2=C(C=CC=C2)C2=C3C(C=CN=C13)=CC1=C2OCO1

Synonyms [en]

Liriodenine; Oxoushinsunine; Micheline B; Spermatheridine; 8H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one; NCI60_042088

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Liriodenine. 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: BioCAD00000013422). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Liriodenine, also known as oxoushinsunine or micheline b, is a member of the class of compounds known as aporphines. Aporphines are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Liriodenine is practically insoluble (in water) and a strong basic compound (based on its pKa). Liriodenine can be found in cherimoya and custard apple, which makes liriodenine a potential biomarker for the consumption of these food products. Liriodenine is a bio-active isolate of the Chinese medicinal herb Zanthoxylum nitidum .

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 475-75-2
  • PubChem: 10144
  • ChEBI: ChEBI:70649
  • HMDB: HMDB0301844
  • KEGG: C09567
  • NCBI MeSH: liriodenine
  • Wikipedia: Liriodenine
  • RefMet: RM0136933
  • MoNA: PM013511
  • Metlin: METLIN_67809
  • Coconut NaturalProduct: CNP0321376.0

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

  1. Absidia orchidis [ncbi taxid: ]
  2. Aconitum vilmorini [ncbi taxid: ]
  3. Aglaia archboldiana [ncbi taxid: 306492]
  4. Allium fistulosum [ncbi taxid: 35875]
  5. Alphonsea mollis [ncbi taxid: 1679248]
  6. Alpinia flabellata [ncbi taxid: 299923]
  7. Alstonia angustiloba [ncbi taxid: 1504383]
  8. Alstonia villosa [ncbi taxid: ]
  9. Alternaria bataticola [ncbi taxid: 48094]
  10. Anagallis monelli [ncbi taxid: ]
  11. Anemone anhuiensis [ncbi taxid: ]
  12. Angelica japonica [ncbi taxid: 265806]
  13. Anisocycla racemosa [ncbi taxid: ]
  14. Annona bullata [ncbi taxid: ]
  15. Annona cherimola [ncbi taxid: 49314]
  16. Annona cherimolia [ncbi taxid: ]
  17. Annona dioica [ncbi taxid: 2986273]
  18. Annona foetida [ncbi taxid: 1937578]
  19. Annona glabra [ncbi taxid: 301703]
  20. Annona montana [ncbi taxid: 49857]
  21. Annona purpurea [ncbi taxid: 1123437]
  22. Annona reticulata [ncbi taxid: 301862]
  23. Annona senegalensis [ncbi taxid: 306945]
  24. Annona squamosa [ncbi taxid: 301693]
  25. Anthemis cotula [ncbi taxid: 158220]
  26. Aquilaria agallocha [ncbi taxid: ]
  27. Aquilaria agallochum [ncbi taxid: 1472648]
  28. Ardisia hortorum [ncbi taxid: ]
  29. Artabotrys hexapetalus [ncbi taxid: 225833]
  30. Artabotrys uncinatus [ncbi taxid: ]
  31. Artemisia pectinata [ncbi taxid: ]
  32. Aspergillus microcysticus [ncbi taxid: 176174]
  33. Aspergillus subolivaceus [ncbi taxid: 41060]
  34. Atherosperma moschatum [ncbi taxid: 88856]
  35. Atrabotrys maingayi [ncbi taxid: ]
  36. Avena fatua [ncbi taxid: 4499]
  37. Baccharis grandicapitulata [ncbi taxid: ]
  38. Baccharis scoparia [ncbi taxid: ]
  39. Baccharis truncata [ncbi taxid: 2707840]
  40. Beesia calthifolia [ncbi taxid: 78478]
  41. Benincasa hispida [ncbi taxid: 102211]
  42. Bipolaris sacchari [ncbi taxid: 48696]
  43. Boschniakia rossica [ncbi taxid: 48555]
  44. Botrychium ternatum [ncbi taxid: 208695]
  45. Briareum asbestinum [ncbi taxid: 86543]
  46. Bupleurum gerardi [ncbi taxid: ]
  47. Bursera kerberi [ncbi taxid: 80313]
  48. Callyspongia spinosissima [ncbi taxid: ]
  49. Camoensia maxima [ncbi taxid: ]
  50. Cardiopetalum calophyllum [ncbi taxid: 2025453]
  51. Centaurea benedicta [ncbi taxid: 50282]
  52. Cheimophila salicella [ncbi taxid: ]
  53. Chloranthus fortunei [ncbi taxid: 146540]
  54. Chuquiraga erinacea [ncbi taxid: 171762]
  55. Cinchona rosulenta [ncbi taxid: ]
  56. Cirsium rivulare [ncbi taxid: 1532346]
  57. Cissampelos sympodialis [ncbi taxid: ]
  58. Citrus wilsonii [ncbi taxid: 475932]
  59. Cleistopholis patens [ncbi taxid: 2708762]
  60. Clerodendrum trichotomum [ncbi taxid: 54229]
  61. Clinacanthus nutans [ncbi taxid: 714457]
  62. Clinopodium acinos [ncbi taxid: 306377]
  63. Coffea liberica var. dewevrei [ncbi taxid: 213301]
  64. Combretum griffithii [ncbi taxid: ]
  65. Conus gladiator [ncbi taxid: 257327]
  66. Costasiella ocellifera [ncbi taxid: 380564]
  67. Creosphaeria sassafras [ncbi taxid: 110550]
  68. Crotalaria stolzii [ncbi taxid: 1977610]
  69. Cucurbita pepo [ncbi taxid: 3663]
  70. Cuphea hyssopifolia [ncbi taxid: 376207]
  71. Curcuma aeruginosa [ncbi taxid: 136205]
  72. Cystoseira barbatula [ncbi taxid: ]
  73. Delisea elegans [ncbi taxid: ]
  74. Delphinium giraldii [ncbi taxid: ]
  75. Desmos longifolia [ncbi taxid: ]
  76. Dictyodendrilla cavernosa [ncbi taxid: 1162782]
  77. Dilophus guineensis [ncbi taxid: ]
  78. Diospyros consolatae [ncbi taxid: 413732]
  79. Disepalum pulchrum [ncbi taxid: 690737]
  80. Doronicum grandiflorum [ncbi taxid: 118763]
  81. Duguetia obovata [ncbi taxid: ]
  82. Echinoclathria subhispida [ncbi taxid: ]
  83. Eliokarmos thyrsoides [ncbi taxid: ]
  84. Emericellopsis minima [ncbi taxid: 45245]
  85. Eminium lehmannii [ncbi taxid: ]
  86. Enantia chlorantha [ncbi taxid: ]
  87. Epimedium grandiflorum [ncbi taxid: 244027]
  88. Eria rigida [ncbi taxid: ]
  89. Eucalyptus albens [ncbi taxid: 183809]
  90. Eucalyptus cneorifolia [ncbi taxid: 1711222]
  91. Euclea pseudebenus [ncbi taxid: 570499]
  92. Euonymus fortunei [ncbi taxid: 255352]
  93. Euphorbia characias subsp. wulfenii [ncbi taxid: 526192]
  94. Euphorbia palustris [ncbi taxid: 492572]
  95. Euphorbia pithyusa [ncbi taxid: 1087776]
  96. Euphorbia sikkimensis [ncbi taxid: ]
  97. Euploca racemosa [ncbi taxid: 1799586]
  98. Farfugium japonicum [ncbi taxid: 186951]
  99. Fissistigma glaucescens [ncbi taxid: 296847]
  100. Flindersia amboinensis [ncbi taxid: 67922]
  101. Fouquieria diguetii [ncbi taxid: 98240]
  102. Fritillaria hupehensis [ncbi taxid: 152089]
  103. Goniothalamus amuyon [ncbi taxid: 1602035]
  104. Goniothalamus scortephanine [ncbi taxid: ]
  105. Goniothalamus topis [ncbi taxid: ]
  106. Guatteria friesiana [ncbi taxid: 402569]
  107. guatteria hispida [ncbi taxid: 402570]
  108. Guatteria multivenia [ncbi taxid: 295175]
  109. Guatteria oliviformis [ncbi taxid: 295178]
  110. guatteria scbmburgkiana [ncbi taxid: ]
  111. Guatteriopsis friesiana [ncbi taxid: ]
  112. Gutierrezia dracunculoides [ncbi taxid: ]
  113. Gymnacranthera paniculata [ncbi taxid: 1085445]
  114. Gynoxys verrucosa [ncbi taxid: ]
  115. Hedysarum gmelini [ncbi taxid: ]
  116. Helenium integrifolium [ncbi taxid: ]
  117. Helichrysum fulvum [ncbi taxid: ]
  118. Holarrhena floribunda [ncbi taxid: 2708850]
  119. Holothuria squamifera [ncbi taxid: ]
  120. Hosta sieboldii [ncbi taxid: 82205]
  121. Hypogymnia vittata [ncbi taxid: 315943]
  122. Illigera luzonensis [ncbi taxid: 74946]
  123. Indigofera arrecta [ncbi taxid: 198859]
  124. Jatropha mahafalensis [ncbi taxid: ]
  125. Juniperus scopulorum [ncbi taxid: 466205]
  126. Karenia mikimotoi [ncbi taxid: 225107]
  127. Laserpitium siler [ncbi taxid: ]
  128. Lasianthaea podocephala [ncbi taxid: ]
  129. Lathyrus latifolius [ncbi taxid: 154494]
  130. Laurelia sempervirens [ncbi taxid: 63809]
  131. Leibnitzia anandria [ncbi taxid: 41596]
  132. Lettowianthus stellatus [ncbi taxid: 489335]
  133. Leucanthemum vulgare [ncbi taxid: 99072]
  134. Liriodendron tulipfera [ncbi taxid: ]
  135. Liriodendron tulipifera [ncbi taxid: 3415]
  136. Lithocarpus haipinii [ncbi taxid: 2738889]
  137. Lobophytum strictum [ncbi taxid: 358786]
  138. Lora quadra [ncbi taxid: ]
  139. Lupinus cosentinii [ncbi taxid: 53222]
  140. Magnolia abovata [ncbi taxid: ]
  141. Magnolia baillonii [ncbi taxid: 86754]
  142. Magnolia champaca [ncbi taxid: 86757]
  143. Magnolia coco [ncbi taxid: 85854]
  144. Magnolia grandiflora [ncbi taxid: 3406]
  145. Magnolia obovata [ncbi taxid: 349509]
  146. Magnolia odora [ncbi taxid: 86770]
  147. Mamestra brassicae [ncbi taxid: 55057]
  148. Melampodium leucanthum [ncbi taxid: 183048]
  149. Michelia alba [ncbi taxid: ]
  150. Michelia champaca [ncbi taxid: ]
  151. Michelia lanuginosa [ncbi taxid: ]
  152. Micheliachampaca [ncbi taxid: ]
  153. Michellia alba [ncbi taxid: ]
  154. Michellia champaca [ncbi taxid: ]
  155. Microcos paniculata [ncbi taxid: 197124]
  156. Micromonospora echinospora [ncbi taxid: 1877]
  157. miliusa cf. banacea [ncbi taxid: ]
  158. Miliusa cuneata [ncbi taxid: 235751]
  159. Miliusa velutina [ncbi taxid: 235758]
  160. Mitrephora glabra [ncbi taxid: 580318]
  161. Moesziomyces antarcticus [ncbi taxid: 84753]
  162. Morella pensylvanica [ncbi taxid: 1155552]
  163. Mortonia palmeri [ncbi taxid: ]
  164. Mucor spinosus [ncbi taxid: 562977]
  165. Mycale mytilorum [ncbi taxid: ]
  166. Nelumbo nucifera [ncbi taxid: 4432]
  167. Neolitsea acuminatissima [ncbi taxid: 2803928]
  168. Niphates rowi [ncbi taxid: ]
  169. Nonomuraea spiralis [ncbi taxid: 46182]
  170. Oncodostigma monosperma [ncbi taxid: ]
  171. Ononis viscosa [ncbi taxid: 798056]
  172. Ormosia dasycarpa [ncbi taxid: ]
  173. Oxytropis lanata [ncbi taxid: 1527600]
  174. Papaver caucasicum [ncbi taxid: ]
  175. Papaver pseudocanescens [ncbi taxid: ]
  176. Parectatosoma mocquerysi [ncbi taxid: 1702145]
  177. Passiflora hybrid [ncbi taxid: ]
  178. Pedicularis rex [ncbi taxid: 321410]
  179. Pellacalyx axillaris [ncbi taxid: 106625]
  180. Pestalotiopsis oenotherae [ncbi taxid: ]
  181. Phlebia strigosozonata [ncbi taxid: ]
  182. Phlomis crinita [ncbi taxid: 316267]
  183. Phyllobates bicolor [ncbi taxid: 92726]
  184. Physalis coztomatl [ncbi taxid: 304143]
  185. Pinus edulis [ncbi taxid: 3340]
  186. Piper brachystachyum [ncbi taxid: 2974510]
  187. Piper sylvaticum [ncbi taxid: 405345]
  188. Piptostigma fugax [ncbi taxid: 2986207]
  189. Plectranthus crassus [ncbi taxid: ]
  190. Podocarpus nubigenus [ncbi taxid: 120627]
  191. Polyalthia cerasoides [ncbi taxid: ]
  192. Polyalthia insignis [ncbi taxid: 1310105]
  193. Polyalthia longifolia [ncbi taxid: ]
  194. Polyalthia macropoda [ncbi taxid: ]
  195. Polyalthia microtus [ncbi taxid: 2306826]
  196. Polyalthia stenopetala [ncbi taxid: 235812]
  197. Polymastia boletiformis [ncbi taxid: 942651]
  198. Populus balsamifera [ncbi taxid: 73824]
  199. Porcelia macrocarpa [ncbi taxid: 2873998]
  200. Posidonia oceanica [ncbi taxid: 55489]
  201. Pseudocyphellaria australiensis [ncbi taxid: ]
  202. Pseudocyphellaria coronata [ncbi taxid: ]
  203. Psidium acutangulum [ncbi taxid: 1835410]
  204. Pterocarpus erinaceus [ncbi taxid: 1071183]
  205. Pyrus bourgaeana [ncbi taxid: 2720245]
  206. Renealmia alpinia [ncbi taxid: 199658]
  207. Rhododendron mucronulatum [ncbi taxid: 105903]
  208. Rumex japonicus [ncbi taxid: 174651]
  209. Salvia amplexicaulis [ncbi taxid: 268888]
  210. Salvia broussonetii [ncbi taxid: 1520014]
  211. Sandoricum koetjape [ncbi taxid: 356285]
  212. Sapranthus palanga [ncbi taxid: 1129707]
  213. Sarcophyton flexuosum [ncbi taxid: 358802]
  214. Sargassum fulvellum [ncbi taxid: 3016]
  215. Sedum sarmentosum [ncbi taxid: 91146]
  216. Selinum libanotis [ncbi taxid: ]
  217. Senecio congestus [ncbi taxid: ]
  218. Shigella boydii [ncbi taxid: 621]
  219. Sibthorpia europaea [ncbi taxid: 165320]
  220. Sideritis dasygnaphala [ncbi taxid: 193331]
  221. Sigillina signifera [ncbi taxid: 440060]
  222. Siparuna tonduziana [ncbi taxid: ]
  223. Sorbus torminalis [ncbi taxid: ]
  224. Sphaerophysa salsula [ncbi taxid: 47651]
  225. Spongia vaginalis [ncbi taxid: ]
  226. Stachyurus praecox [ncbi taxid: 85277]
  227. Stellaria media [ncbi taxid: 13274]
  228. Stemona tuberosa [ncbi taxid: 167572]
  229. Stephania dinklagei [ncbi taxid: ]
  230. Stevia pilosa [ncbi taxid: 558497]
  231. Streptomyces melanogenes [ncbi taxid: 67326]
  232. Streptomyces parvisporogenes [ncbi taxid: 68252]
  233. Strychnos gossweileri [ncbi taxid: ]
  234. Suaeda maritima [ncbi taxid: 126913]
  235. Syzygium formosanum [ncbi taxid: 1609897]
  236. Talauma gitigensis [ncbi taxid: ]
  237. Talauma mexicana Don. [ncbi taxid: ]
  238. Teclea verdoorniana [ncbi taxid: ]
  239. Tephroseris kirilowii [ncbi taxid: 186974]
  240. Thelephora aurantiotincta [ncbi taxid: 654496]
  241. Thioalkalivibrio versutus [ncbi taxid: 106634]
  242. Triunia erythrocarpa [ncbi taxid: ]
  243. Trivalvaria macrophylla [ncbi taxid: 235846]
  244. Tsoomgiodendron odorum [ncbi taxid: ]
  245. Tsoongiodendron odorum [ncbi taxid: ]
  246. Ursinia anethoides [ncbi taxid: ]
  247. Uvaria mocali [ncbi taxid: ]
  248. Verbascum undulatum [ncbi taxid: 3075787]
  249. Xanthium sibiricum [ncbi taxid: 576365]
  250. Xanthorhiza simplicissima [ncbi taxid: 13762]
  251. Xylopia aethiopica [ncbi taxid: 1317910]
  252. Zanthoxylum caudatum [ncbi taxid: ]
  253. Zanthoxylum Cuspi [ncbi taxid: ]
  254. Zanthoxylum cuspidatum [ncbi taxid: ]
  255. Zanthoxylum nitidum [ncbi taxid: 354528]
  256. Zanthoxylum tetraspermum [ncbi taxid: ]
  257. Zephyranthes flava [ncbi taxid: ]

Pathway Synthetic

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