Cycloartenol (BioCAD00000009109)

plant natural products microbial natural products

Metabolite Card

Formula: C30H50O (426.3861)
SMILES: [H][C@@]1(CC[C@@]2(C)[C@]3([H])CC[C@]4([H])[C@]5(C[C@@]35CC[C@]12C)CC[C@H](O)C4(C)C)[C@H](C)CCC=C(C)C

Synonyms [en]

cycloartenol; 9beta,19-cyclolanost-24-en-3beta-ol; 9beta,19-cyclo-24-lanosten-3beta-ol; cycloart-24(25)-enol; (3beta,9beta)-9,19-cyclolanost-24-en-3-ol; cycloarterenol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Cycloartenol. 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: BioCAD00000009109). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Cycloartenol is found in alcoholic beverages. Cycloartenol is a constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato) Cycloartenol is a sterol precursor in photosynthetic organisms and plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene. Its structure is also related to triterpenoid lanosterol

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 469-38-5
  • PubChem: 382580
  • PubChem: 92110
  • ChEBI: ChEBI:17030
  • ChEBI: ChEBI:173045
  • HMDB: HMDB0036591
  • LipidMaps: LMST01100008
  • KEGG: C01902
  • BioCyc: CYCLOARTENOL
  • NCBI MeSH: cycloartenol
  • Wikipedia: Cycloartenol
  • RefMet: RM0126042
  • Metlin: METLIN_34476
  • Coconut NaturalProduct: CNP0224096.11
  • Coconut NaturalProduct: CNP0224096.13
  • Coconut NaturalProduct: CNP0224096.14
  • Coconut NaturalProduct: CNP0224096.7
  • Coconut NaturalProduct: CNP0224096.8
  • Coconut NaturalProduct: CNP0224096.9
  • Coconut NaturalProduct: CNP0309728.2

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03200 5.4.99.8 (S)-2,3-epoxysqualene mutase (cyclizing, cycloartenol-forming)
KEGG:R03765 C01902<=>C05437
KEGG:R05760 S-adenosyl-L-methionine:cycloartenol 24-C-methyltransferase
KEGG:R07481 2.1.1.41 C01902 + C00019<=>C08830 + C00021
KEGG:R12458 2.1.1.142 S-adenosyl-L-methionine:cycloartenol 24-C-methyltransferase
Rhea:RHEA:13138 2.1.1.142 cycloartenol + S-adenosyl-L-methionine => cyclolaudenol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:13139 2.1.1.142 cyclolaudenol + S-adenosyl-L-homocysteine + H+ => cycloartenol + S-adenosyl-L-methionine
Rhea:RHEA:13140 2.1.1.142 cycloartenol + S-adenosyl-L-methionine <=> cyclolaudenol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:21309 5.4.99.8 (S)-2,3-epoxysqualene => cycloartenol
Rhea:RHEA:21310 5.4.99.8 cycloartenol => (S)-2,3-epoxysqualene
Rhea:RHEA:21311 5.4.99.8 (S)-2,3-epoxysqualene <=> cycloartenol
Rhea:RHEA:59013 2.1.1.41 cycloartenol + S-adenosyl-L-methionine => 24-methylenecycloartanol + S-adenosyl-L-homocysteine + H+
Rhea:RHEA:59014 2.1.1.41 24-methylenecycloartanol + S-adenosyl-L-homocysteine + H+ => cycloartenol + S-adenosyl-L-methionine
Rhea:RHEA:59015 2.1.1.41 cycloartenol + S-adenosyl-L-methionine <=> 24-methylenecycloartanol + S-adenosyl-L-homocysteine + H+
BioCyc:CYCLOARTENOL-SYNTHASE-RXN 5.4.99.8 EPOXYSQUALENE --> CYCLOARTENOL
BioCyc:RXN-21829 1.14.18.10 CYCLOARTENOL + 6 FERROCYTOCHROME-B5 + 3 OXYGEN-MOLECULE + 5 PROTON --> CPD-23708 + 6 FERRICYTOCHROME-B5 + 4 WATER
BioCyc:RXN-4021 2.1.1.41 S-ADENOSYLMETHIONINE + CYCLOARTENOL --> PROTON + ADENOSYL-HOMO-CYS + CPD-696
BioCyc:2.1.1.142-RXN 2.1.1.142 S-ADENOSYLMETHIONINE + CYCLOARTENOL --> ADENOSYL-HOMO-CYS + CPD-22096 + PROTON
BioCyc:RXN-4282 1.3.1.72 CYCLOARTENOL + NADPH + PROTON --> CPD-4181 + NADP
BioCyc:RXN-11875 2.1.1.- CPD-12850 + Methylated-methyl-acceptors --> CYCLOARTENOL + Demethylated-methyl-acceptors
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Organism Source

Taxonomy Source

  1. Abrus precatorius [ncbi taxid: 3816]
  2. Capsicum annuum [ncbi taxid: 4072]
  3. Cimicifuga foetida [ncbi taxid: ]
  4. Citrus chachiensis [ncbi taxid: ]
  5. Citrus reticulata [ncbi taxid: 85571]
  6. Euphorbia antiquorum [ncbi taxid: 334664]
  7. Euphorbia ebracteolata [ncbi taxid: 526193]
  8. Euphorbia fischeriana [ncbi taxid: 1035560]
  9. Euphorbia hirta [ncbi taxid: 318062]
  10. Euphorbia pekinensis [ncbi taxid: 273621]
  11. Glycine max [ncbi taxid: 3847]
  12. Hippophae rhamnoides [ncbi taxid: 193516]
  13. Nicotiana tabacum [ncbi taxid: 4097]
  14. Papaver somniferum [ncbi taxid: 3469]
  15. Physalis alkekengi var. franchetii [ncbi taxid: ]
  16. Pinellia ternata [ncbi taxid: 199225]
  17. Radix euphorbiae pekinensis [ncbi taxid: ]
  18. Ulva lactuca [ncbi taxid: 63410]
  19. Ulva pertusa [ncbi taxid: 3120]
  20. Arabidopsis thaliana [ncbi taxid: 3702]
  21. Artocarpus integrifolia [ncbi taxid: ]
  22. Casearia ilicifolia [ncbi taxid: ]
  23. Digitalis lanata Ehrh. [ncbi taxid: ]
  24. Euphorbia guyoniana [ncbi taxid: 1138347]
  25. Euphorbia neriifolia [ncbi taxid: 334689]
  26. Euphorbia peplus [ncbi taxid: 38846]
  27. Euphorbia petiolata [ncbi taxid: 212954]
  28. Euphorbia segetalis [ncbi taxid: 38847]
  29. Glycine max [ncbi taxid: 3847]
  30. Linum usitatissimum [ncbi taxid: 4006]
  31. Nicotiana benthamiana [ncbi taxid: 4100]
  32. Pedilanthus tithymaloides [ncbi taxid: ]
  33. Populus tremula L. [ncbi taxid: ]
  34. Santolina rosmarinifolia subsp. canescens [ncbi taxid: ]
  35. Solanum tuberosum [ncbi taxid: 4113]
  36. Swietenia mahogani [ncbi taxid: ]
  37. Capsicum annuum [ncbi taxid: 4072]
  38. Euphorbia ebracteolata [ncbi taxid: 526193]
  39. Euphorbia fischeriana [ncbi taxid: 1035560]
  40. Euphorbia hirta [ncbi taxid: 318062]
  41. Hippophae rhamnoides [ncbi taxid: 193516]
  42. Pinellia ternata [ncbi taxid: 199225]
  43. Capsicum annuum [ncbi taxid: 4072]
  44. Euphorbia ebracteolata [ncbi taxid: 526193]
  45. Euphorbia fischeriana [ncbi taxid: 1035560]
  46. Euphorbia hirta [ncbi taxid: 318062]
  47. Hippophae rhamnoides [ncbi taxid: 193516]
  48. Pinellia ternata [ncbi taxid: 199225]
  49. Aaptos aaptos [ncbi taxid: 253165]
  50. Abrus precatorius [ncbi taxid: 3816]
  51. Acer pycnanthum [ncbi taxid: 349748]
  52. Aconitum nevadense [ncbi taxid: 2739826]
  53. Adiantum caudatum [ncbi taxid: 1073774]
  54. Agathosma betulina [ncbi taxid: 501610]
  55. Aglaia lawii [ncbi taxid: 306522]
  56. Ajuga reptans [ncbi taxid: 38596]
  57. Aloe microstigma [ncbi taxid: 1128801]
  58. Alseodaphne corneri [ncbi taxid: ]
  59. Amaioua guianensis [ncbi taxid: 136670]
  60. Amberboa ramosa [ncbi taxid: ]
  61. Andira paruiflora [ncbi taxid: ]
  62. Annona impressivenia [ncbi taxid: ]
  63. Antitrogus consanguineus [ncbi taxid: 272057]
  64. Aplidium multiplicatum [ncbi taxid: 3106037]
  65. Arnica sachalinensis [ncbi taxid: 436212]
  66. Aspergillus unguis [ncbi taxid: 40381]
  67. Aulacocephalus temmincki [ncbi taxid: ]
  68. Baccharis santelicis [ncbi taxid: 1654449]
  69. Berberis aquifolium [ncbi taxid: 203270]
  70. Berchemia floribunda [ncbi taxid: 1226760]
  71. Bersama yangambiensis [ncbi taxid: ]
  72. Betula maximowicziana [ncbi taxid: 211500]
  73. Brya ebenus [ncbi taxid: 77267]
  74. Bryum rutilans [ncbi taxid: ]
  75. Bugula neritina [ncbi taxid: 10212]
  76. Calanthe arisanensis [ncbi taxid: 309525]
  77. Calotropis gigantea [ncbi taxid: 4066]
  78. Capsicum annuum [ncbi taxid: 4072]
  79. Castanopsis sclerophylla [ncbi taxid: 425823]
  80. Centaurea napifolia [ncbi taxid: 363436]
  81. Channa argus [ncbi taxid: 215402]
  82. Choisya arizonica [ncbi taxid: ]
  83. Chrozophora prostrata [ncbi taxid: ]
  84. Chrysosplenium oppositifolium [ncbi taxid: 1155259]
  85. Citrus chachiensis [ncbi taxid: ]
  86. Comamonas testosteroni [ncbi taxid: 285]
  87. Conocephalum japonicum [ncbi taxid: 134427]
  88. Cordylanthus kingii [ncbi taxid: 90354]
  89. Corydalis taliensis [ncbi taxid: 54424]
  90. Crinipellis scabella [ncbi taxid: 230788]
  91. Croton cumingii [ncbi taxid: ]
  92. Cystophora scalaris [ncbi taxid: 590105]
  93. Diplopteraster multipes [ncbi taxid: 465783]
  94. Diploschistes cretaceus [ncbi taxid: ]
  95. Disynaphia halimifolia [ncbi taxid: ]
  96. Doodia picta [ncbi taxid: ]
  97. Elaeagnus angustifolia [ncbi taxid: 36777]
  98. Epimedium sagittatum [ncbi taxid: 253616]
  99. Eragrostis viscosa [ncbi taxid: 2575316]
  100. Eriocephalus scariosus [ncbi taxid: ]
  101. Eriogonum nudum [ncbi taxid: 430753]
  102. Erythrina sandwicensis [ncbi taxid: 2590719]
  103. Eunicella cavolinii [ncbi taxid: ]
  104. Euphorbia balsamifera [ncbi taxid: 154988]
  105. Euphorbia ebracteolata [ncbi taxid: 526193]
  106. Euphorbia fischeriana [ncbi taxid: 1035560]
  107. Euphorbia guyoniana [ncbi taxid: 1138347]
  108. Euphorbia hirta [ncbi taxid: 318062]
  109. Euphorbia neriifolia [ncbi taxid: 334689]
  110. Ficus macrophylla [ncbi taxid: 182117]
  111. Forsteronia refracta [ncbi taxid: 387687]
  112. Fridericia chica [ncbi taxid: 353936]
  113. Girgensohnia diptera [ncbi taxid: 1665486]
  114. Glycine max [ncbi taxid: 3847]
  115. Gmelina arborea [ncbi taxid: 201509]
  116. Grewia mollis [ncbi taxid: 3105936]
  117. Gymnocarpium robertianum [ncbi taxid: 983334]
  118. Haminoea orbignyana [ncbi taxid: 489901]
  119. Hedysarum multijugum [ncbi taxid: ]
  120. Heliotropium floridum [ncbi taxid: 454097]
  121. Hepialus hecta [ncbi taxid: ]
  122. Heterotheca grandiflora [ncbi taxid: 1573925]
  123. Hippophae rhamnoides [ncbi taxid: 193516]
  124. Hornschuchia citriodora [ncbi taxid: 306963]
  125. Hovenia acerba [ncbi taxid: 210357]
  126. Hyacinthoides hispanica [ncbi taxid: 81759]
  127. Hydnocarpus octandra [ncbi taxid: ]
  128. Hygrophila polysperma [ncbi taxid: 693374]
  129. Incarvillea emodi [ncbi taxid: 291311]
  130. Juglans nigra [ncbi taxid: 16719]
  131. Kaempferia marginata [ncbi taxid: 340432]
  132. Kaunia saltensis [ncbi taxid: 1745086]
  133. Knema attenuata [ncbi taxid: 2022737]
  134. Linum usitatissimum [ncbi taxid: 4006]
  135. Macfadyena cynanchoides [ncbi taxid: ]
  136. Mangifera indica [ncbi taxid: 29780]
  137. Mcneillia graminifolia [ncbi taxid: 308170]
  138. Meridiastra calcar [ncbi taxid: 46520]
  139. Mucuna sloanei [ncbi taxid: 202240]
  140. Mycale laxissima [ncbi taxid: 458504]
  141. Myelochroa rhytidodes [ncbi taxid: ]
  142. Narcissus concolor [ncbi taxid: 54871]
  143. Nauclea officinalis [ncbi taxid: 1009495]
  144. Nervilia fordii [ncbi taxid: 1168071]
  145. Nicotiana tabacum [ncbi taxid: 4097]
  146. Notholaena peninsularis [ncbi taxid: ]
  147. Ochrocarpos odoratus [ncbi taxid: ]
  148. Oenothera biennis [ncbi taxid: 3942]
  149. Oligonychus bessardi [ncbi taxid: ]
  150. Oncoba echinata [ncbi taxid: ]
  151. Ophiolepis superba [ncbi taxid: 1869291]
  152. Paeonia lactiflora [ncbi taxid: 35924]
  153. Paeonia rockii [ncbi taxid: 62886]
  154. Papaver sommiferum [ncbi taxid: ]
  155. Papaver somniferum [ncbi taxid: 3469]
  156. Papilio phorcas [ncbi taxid: 77261]
  157. Parabenzoin trilobum [ncbi taxid: ]
  158. Pedilanthus tithymaloides [ncbi taxid: ]
  159. Philotheca myoporoides [ncbi taxid: 68542]
  160. Phlomis regelii [ncbi taxid: ]
  161. Pinellia ternata [ncbi taxid: 199225]
  162. Pinus sitchensis [ncbi taxid: ]
  163. Pittosporum viridiflorum [ncbi taxid: 992772]
  164. Plexaurella grisea [ncbi taxid: 204333]
  165. Plumbago zeylanica [ncbi taxid: 76149]
  166. Polycephalomyces nipponicus [ncbi taxid: ]
  167. Pseudocedrela kotschyi [ncbi taxid: 356281]
  168. Pseudonocardia compacta [ncbi taxid: 33911]
  169. Pseudotaxus chienii [ncbi taxid: 89481]
  170. Punctelia microsticta [ncbi taxid: ]
  171. Rabdosia macrocalyx [ncbi taxid: ]
  172. Rhizopogon pumilionus [ncbi taxid: ]
  173. rice bran [ncbi taxid: ]
  174. Roldana barba-johannis [ncbi taxid: 344068]
  175. Roldana sessilifolia [ncbi taxid: 1707486]
  176. Rothmannia urcelliformis [ncbi taxid: 1623657]
  177. Rubrivivax gelatinosus [ncbi taxid: 28068]
  178. Ruta pinnata [ncbi taxid: 452794]
  179. Salvia dorrii [ncbi taxid: 207754]
  180. Santolina rosmarinifolia [ncbi taxid: 99098]
  181. Scutellaria discolor [ncbi taxid: 1383557]
  182. Senecio coahuilensis [ncbi taxid: ]
  183. Senecio othonniformis [ncbi taxid: ]
  184. Serratula xeranthemoides [ncbi taxid: ]
  185. Sinularia manaarensis [ncbi taxid: ]
  186. Smallanthus glabratus [ncbi taxid: ]
  187. Smilax glabra [ncbi taxid: 703614]
  188. Sophora angustifolia [ncbi taxid: ]
  189. Sphaeria biglobosa [ncbi taxid: ]
  190. Sphaeria doliolum [ncbi taxid: ]
  191. Stevia polycephala [ncbi taxid: 558499]
  192. Streptomyces parvisporogenes [ncbi taxid: 68252]
  193. Streptomyces sclerotialus [ncbi taxid: 1957]
  194. Swertia decora [ncbi taxid: 166616]
  195. Teucrium depressum [ncbi taxid: ]
  196. Theonella cupola [ncbi taxid: 1336890]
  197. Thymus piperella [ncbi taxid: ]
  198. Trichilia rubescens [ncbi taxid: 1672008]
  199. Tritomaria quinquedentata [ncbi taxid: ]
  200. Ulva lactuca [ncbi taxid: 63410]
  201. Ulva pertusa [ncbi taxid: 3120]
  202. Unknown sp. [ncbi taxid: ]
  203. Venidium hirsutum [ncbi taxid: ]
  204. Veratrum eschscholtzii [ncbi taxid: ]
  205. Vicoa vestita [ncbi taxid: ]
  206. Xylopia columbiana [ncbi taxid: ]
  207. Zantedeschia aethiopica [ncbi taxid: 69721]
  208. Cyathea podophylla [ncbi taxid: ]

Pathway Synthetic

pathway id name
Plant Reactome:R-HVU-1119370 Sterol biosynthesis
Plant Reactome:R-OAU-2744345 Metabolism and regulation
Plant Reactome:R-TAE-2744344 Secondary metabolism
Plant Reactome:R-TAE-1119370 Sterol biosynthesis
Plant Reactome:R-MES-2744345 Metabolism and regulation
Plant Reactome:R-TDI-2744345 Metabolism and regulation
Plant Reactome:R-DRO-2744345 Metabolism and regulation
Plant Reactome:R-DRO-1119370 Sterol biosynthesis
Plant Reactome:R-GSU-2744344 Secondary metabolism
Plant Reactome:R-PTI-2744345 Metabolism and regulation
Plant Reactome:R-PTI-1119370 Sterol biosynthesis
Plant Reactome:R-GMA-2744345 Metabolism and regulation
Plant Reactome:R-GMA-2744344 Secondary metabolism
Plant Reactome:R-PDA-2744345 Metabolism and regulation
Plant Reactome:R-PVU-2744345 Metabolism and regulation
Plant Reactome:R-BRA-1119370 Sterol biosynthesis
Plant Reactome:R-OPU-1119370 Sterol biosynthesis
Plant Reactome:R-DCA-1119370 Sterol biosynthesis
Plant Reactome:R-CSI-2744345 Metabolism and regulation
Plant Reactome:R-CSI-1119370 Sterol biosynthesis
View All Pathways