(+)-Piperitol (BioCAD00000000209)

plant natural products microbial natural products

Metabolite Card

Formula: C20H20O6 (356.126)
SMILES: COC1=C(C=CC(=C1)[C@@H]2[C@H]3CO[C@@H]([C@H]3CO2)C4=CC5=C(C=C4)OCO5)O

Synonyms [en]

(+)-piperitol; (+)-Regiomontanin; piperitol; Sesamin monocatechol 3-methylate; CLA6B4LBF3; UNII-CLA6B4LBF3

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

(+)-Piperitol. 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: BioCAD00000000209). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

4-[(1S,3aR,4S,6aR)-4-(1,3-benzodioxol-5-yl)tetrahydrofuro[3,4-c]furan-1-yl]-2-methoxyphenol is a furofuran that is tetrahydro-1H,3H-furo[3,4-c]furan which is substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl and 1,3-benzodioxol-5-yl groups, respectively (the 1S,3aR,4S,6aR stereoisomer). The biosynthetic precursor of (+)-sesamin. It has a role as a plant metabolite. It is a furofuran, a lignan, a member of benzodioxoles, an aromatic ether and a member of phenols. Piperitol has been reported in Kuloa usambarensis, Eriosolena composita, and other organisms with data available.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 28115-67-5
  • CAS Registry Number: 52151-92-5
  • CAS Registry Number: 891182-93-7
  • PubChem: 10247670
  • ChEBI: ChEBI:141003
  • KEGG: C21954
  • NCBI MeSH: piperitol
  • Coconut NaturalProduct: CNP0214326.4
  • Coconut NaturalProduct: CNP0248930.1
  • Coconut NaturalProduct: CNP0248930.2
  • Coconut NaturalProduct: CNP0248930.4
  • Coconut NaturalProduct: CNP0248930.5
  • Coconut NaturalProduct: CNP0319543.1
  • Coconut NaturalProduct: CNP0528722.1
  • Coconut NaturalProduct: CNP0528722.2
  • Coconut NaturalProduct: CNP0528722.3
  • Coconut NaturalProduct: CNP0528722.4
  • Coconut NaturalProduct: CNP0539403.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R12153 1.14.19.74 (+)-pinoresinol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
KEGG:R12154 1.14.19.74 (+)-piperitol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
Rhea:RHEA:56777 1.14.19.74 (+)-pinoresinol + reduced [NADPH—hemoprotein reductase] + O2 => (+)-piperitol + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+
Rhea:RHEA:56778 1.14.19.74 (+)-piperitol + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+ => (+)-pinoresinol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:56779 1.14.19.74 (+)-pinoresinol + reduced [NADPH—hemoprotein reductase] + O2 <=> (+)-piperitol + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+
Rhea:RHEA:56781 1.14.19.74 (+)-piperitol + reduced [NADPH—hemoprotein reductase] + O2 => (+)-sesamin + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+
Rhea:RHEA:56782 1.14.19.74 (+)-sesamin + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+ => (+)-piperitol + reduced [NADPH—hemoprotein reductase] + O2
Rhea:RHEA:56783 1.14.19.74 (+)-piperitol + reduced [NADPH—hemoprotein reductase] + O2 <=> (+)-sesamin + oxidized [NADPH—hemoprotein reductase] + 2 H2O + H+
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Organism Source

Taxonomy Source

  1. Actinodaphne longifolia [ncbi taxid: ]
  2. Angelica acutiloba [ncbi taxid: 55605]
  3. Angelica gigas [ncbi taxid: 85712]
  4. Angelica sinensis [ncbi taxid: 165353]
  5. Anthotroche blackii [ncbi taxid: 195725]
  6. Aplophyllum villosum [ncbi taxid: ]
  7. Archaster typicus [ncbi taxid: 136937]
  8. Artemisia argyi [ncbi taxid: 259893]
  9. Artemisia montana [ncbi taxid: 669134]
  10. Artemisia princeps [ncbi taxid: 223870]
  11. Asarum heterotropoides [ncbi taxid: 366663]
  12. Asarum sieboldii [ncbi taxid: 76098]
  13. Asiasarum heterotropoides [ncbi taxid: ]
  14. Asiasarum sieboldii [ncbi taxid: ]
  15. Beaucarnea recurvata [ncbi taxid: 39519]
  16. Centaurea arenaria [ncbi taxid: 1486496]
  17. Cinnamomum camphora [ncbi taxid: 13429]
  18. Citrus maxima [ncbi taxid: 37334]
  19. Clitocybe subilludens [ncbi taxid: ]
  20. Cota saguramica [ncbi taxid: 589833]
  21. Cotylelobium scabriusculum [ncbi taxid: 365534]
  22. Cratystylis conocephala [ncbi taxid: 125682]
  23. Cryptocarya angulata [ncbi taxid: 1118762]
  24. Diospyros abyssinica [ncbi taxid: 413718]
  25. Diospyros elliptifolia [ncbi taxid: 2945281]
  26. Diospyros peregrina [ncbi taxid: ]
  27. Eremophila macdonnellii [ncbi taxid: 378412]
  28. Eucalyptus perriniana [ncbi taxid: 183845]
  29. Gutenbergia cordifolia [ncbi taxid: 1671336]
  30. Helichrysum bracteatum [ncbi taxid: ]
  31. Marsilea quadrifolia [ncbi taxid: 13816]
  32. Mastophora hutchinsoni [ncbi taxid: 2508621]
  33. Mikania scandens [ncbi taxid: 102787]
  34. Myristica fragrans [ncbi taxid: 51089]
  35. Papilio xuthus [ncbi taxid: 66420]
  36. Petrosia volcano [ncbi taxid: ]
  37. Phaeotremella fagi [ncbi taxid: 334123]
  38. Phoma herbarum [ncbi taxid: 73001]
  39. Phyllodium pulchellum [ncbi taxid: 406422]
  40. Pinus parviflora [ncbi taxid: 71644]
  41. Plantago hookeriana [ncbi taxid: 197805]
  42. Scorzonera hispanica [ncbi taxid: ]
  43. Sesamum indicum [ncbi taxid: 4182]
  44. Sesamum orientale [ncbi taxid: ]
  45. Solenostoma triste [ncbi taxid: ]
  46. Streptomyces sp. IT-44 [ncbi taxid: ]
  47. Tolypothrix nodosa [ncbi taxid: 882386]
  48. Trapa japonica [ncbi taxid: 363523]
  49. Tunica prolifera [ncbi taxid: ]
  50. Zanthoxylum bungeanum [ncbi taxid: 328401]
  51. Zanthoxylum petiolare [ncbi taxid: 2099542]
  52. Zanthoxylum piperitum [ncbi taxid: 354529]
  53. Zanthoxylum schinifolium [ncbi taxid: 354530]
  54. Aplophyllum villosum [ncbi taxid: ]
  55. Archaster typicus [ncbi taxid: 136937]
  56. Asarum heterotropoides [ncbi taxid: 366663]
  57. Asarum sieboldii [ncbi taxid: 76098]
  58. Asiasarum heterotropoides [ncbi taxid: ]
  59. Asiasarum sieboldii [ncbi taxid: ]
  60. Beaucarnea recurvata [ncbi taxid: 39519]
  61. Centaurea arenaria [ncbi taxid: 1486496]
  62. Clitocybe subilludens [ncbi taxid: ]
  63. Cotylelobium scabriusculum [ncbi taxid: 365534]
  64. Cratystylis conocephala [ncbi taxid: 125682]
  65. Diospyros abyssinica [ncbi taxid: 413718]
  66. Diospyros elliptifolia [ncbi taxid: 2945281]
  67. Diospyros peregrina [ncbi taxid: ]
  68. Gutenbergia cordifolia [ncbi taxid: 1671336]
  69. Hypoestes purpurea [ncbi taxid: 2803927]
  70. Mikania scandens [ncbi taxid: 102787]
  71. Petrosia volcano [ncbi taxid: ]
  72. Phaeotremella fagi [ncbi taxid: 334123]
  73. Phyllodium pulchellum [ncbi taxid: 406422]
  74. Scorzonera hispanica [ncbi taxid: ]
  75. Trapa japonica [ncbi taxid: 363523]
  76. Zanthoxylum piperitum [ncbi taxid: 354529]
  77. Zanthoxylum wutaiense [ncbi taxid: 697043]
  78. Aconitum episcopale [ncbi taxid: 226106]
  79. Aplophyllum villosum [ncbi taxid: ]
  80. Archaster typicus [ncbi taxid: 136937]
  81. Ardisia arborescens [ncbi taxid: ]
  82. Aromia moschata [ncbi taxid: 1265417]
  83. Asarum heterotropoides [ncbi taxid: 366663]
  84. Asarum sieboldii [ncbi taxid: 76098]
  85. Asiasarum heterotropoides [ncbi taxid: ]
  86. Asiasarum sieboldii [ncbi taxid: ]
  87. Beaucarnea recurvata [ncbi taxid: 39519]
  88. Cacia concinna [ncbi taxid: ]
  89. Centaurea arenaria [ncbi taxid: 1486496]
  90. Clitocybe subilludens [ncbi taxid: ]
  91. Cotylelobium scabriusculum [ncbi taxid: 365534]
  92. Cratystylis conocephala [ncbi taxid: 125682]
  93. Diospyros abyssinica [ncbi taxid: 413718]
  94. Diospyros elliptifolia [ncbi taxid: 2945281]
  95. Diospyros peregrina [ncbi taxid: ]
  96. Eucalyptus hybrid [ncbi taxid: ]
  97. Garcinia oligantha [ncbi taxid: ]
  98. Gutenbergia cordifolia [ncbi taxid: 1671336]
  99. Iris spuria [ncbi taxid: 93026]
  100. Mikania scandens [ncbi taxid: 102787]
  101. Pagrus major [ncbi taxid: 143350]
  102. Parmelia vittata [ncbi taxid: ]
  103. Petrosia volcano [ncbi taxid: ]
  104. Phaeotremella fagi [ncbi taxid: 334123]
  105. Phyllodium pulchellum [ncbi taxid: 406422]
  106. Pocillopora damicornis [ncbi taxid: 46731]
  107. Protaetia cuprea [ncbi taxid: 360077]
  108. Rubus trifidus [ncbi taxid: 75096]
  109. Scorzonera hispanica [ncbi taxid: ]
  110. Trapa japonica [ncbi taxid: 363523]
  111. Zanthoxylum piperitum [ncbi taxid: 354529]
  112. Angelica acutiloba [ncbi taxid: 55605]
  113. Angelica gigas [ncbi taxid: 85712]
  114. Angelica sinensis [ncbi taxid: 165353]
  115. Aplophyllum villosum [ncbi taxid: ]
  116. Archaster typicus [ncbi taxid: 136937]
  117. Artemisia argyi [ncbi taxid: 259893]
  118. Artemisia montana [ncbi taxid: 669134]
  119. Artemisia princeps [ncbi taxid: 223870]
  120. Asarum heterotropoides [ncbi taxid: 366663]
  121. Asarum sieboldii [ncbi taxid: 76098]
  122. Asiasarum heterotropoides [ncbi taxid: ]
  123. Asiasarum sieboldii [ncbi taxid: ]
  124. Beaucarnea recurvata [ncbi taxid: 39519]
  125. Centaurea arenaria [ncbi taxid: 1486496]
  126. Cinnamomum camphora [ncbi taxid: 13429]
  127. Citrus maxima [ncbi taxid: 37334]
  128. Clitocybe subilludens [ncbi taxid: ]
  129. Cotylelobium scabriusculum [ncbi taxid: 365534]
  130. Cratystylis conocephala [ncbi taxid: 125682]
  131. Diospyros abyssinica [ncbi taxid: 413718]
  132. Diospyros elliptifolia [ncbi taxid: 2945281]
  133. Diospyros peregrina [ncbi taxid: ]
  134. Gutenbergia cordifolia [ncbi taxid: 1671336]
  135. Mikania scandens [ncbi taxid: 102787]
  136. Myristica fragrans [ncbi taxid: 51089]
  137. Petrosia volcano [ncbi taxid: ]
  138. Phaeotremella fagi [ncbi taxid: 334123]
  139. Phyllodium pulchellum [ncbi taxid: 406422]
  140. Scorzonera hispanica [ncbi taxid: ]
  141. Sesamum indicum [ncbi taxid: 4182]
  142. Sesamum orientale [ncbi taxid: ]
  143. Trapa japonica [ncbi taxid: 363523]
  144. Zanthoxylum bungeanum [ncbi taxid: 328401]
  145. Zanthoxylum piperitum [ncbi taxid: 354529]
  146. Zanthoxylum schinifolium [ncbi taxid: 354530]
  147. Andinobates fulguritus [ncbi taxid: 111124]
  148. Catalpa bignonioides [ncbi taxid: 85179]
  149. Cephalonoplos segetum [ncbi taxid: 41543]
  150. Comaster multifida [ncbi taxid: ]
  151. Esenbeckia nesiotica [ncbi taxid: ]
  152. Helipterum tenellum [ncbi taxid: ]
  153. Hyptis tomentosa [ncbi taxid: ]
  154. Ipomoea cristulata [ncbi taxid: 1917418]
  155. Lachnoanaerobaculum saburreum [ncbi taxid: 467210]
  156. Lens phaseoloides [ncbi taxid: ]
  157. Lophozonia menziesii [ncbi taxid: ]
  158. Machilus odoratissima [ncbi taxid: ]
  159. Machilus odoratissima NEES [ncbi taxid: ]
  160. Myristica fragrans [ncbi taxid: 51089]
  161. Pancratium trianthum [ncbi taxid: 1055008]
  162. Piper pedicellosum [ncbi taxid: 2231266]
  163. Rhodotypos scandens [ncbi taxid: 32245]
  164. Saussurea lappa [ncbi taxid: ]
  165. Xanthostemon oppositifolius [ncbi taxid: 1619564]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5469 sesamin biosynthesis
BioCyc:ARA_PWY-5469 sesamin biosynthesis
PlantCyc:ALYRATA_PWY-5469 sesamin biosynthesis
PlantCyc:SWITCHGRASS_PWY-5469 sesamin biosynthesis
PlantCyc:TPARVULA_PWY-5469 sesamin biosynthesis
PlantCyc:ASPARAGUS_PWY-5469 sesamin biosynthesis
PlantCyc:BARLEY_PWY-5469 sesamin biosynthesis
PlantCyc:BRACHYPODIUM_PWY-5469 sesamin biosynthesis
PlantCyc:BRAPA_FPSC_PWY-5469 sesamin biosynthesis
PlantCyc:BSTRICTA_PWY-5469 sesamin biosynthesis
PlantCyc:CARIETINUM_ICC4958_PWY-5469 sesamin biosynthesis
PlantCyc:DROTUNDATA_PWY-5469 sesamin biosynthesis
PlantCyc:HOP_PWY-5469 sesamin biosynthesis
PlantCyc:KFEDTSCHENKOI_PWY-5469 sesamin biosynthesis
PlantCyc:LPERRIERI_PWY-5469 sesamin biosynthesis
PlantCyc:NTABACUM_TN90_PWY-5469 sesamin biosynthesis
PlantCyc:OILSEEDRAPE_PWY-5469 sesamin biosynthesis
PlantCyc:PAXILLARIS_PWY-5469 sesamin biosynthesis
PlantCyc:PHALLII_PWY-5469 sesamin biosynthesis
PlantCyc:PPERSICA_PWY-5469 sesamin biosynthesis
View All Pathways