Sesamin (BioCAD00000017716)

blood

Metabolite Card

Formula: C20H18O6 (354.1103)
SMILES: [H][C@]12CO[C@H](C3=CC4=C(OCO4)C=C3)[C@@]1([H])CO[C@@H]2C1=CC2=C(OCO2)C=C1

Synonyms [en]

sesamin; (+)-Sesamin; Sezamin; Fagarol; 5,5'-(1S,3aR,4S,6aR)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diylbis(1,3-benzodioxole); epi-sesamin

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Sesamin. 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: BioCAD00000017716). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

(+)-Sesamin, also known as fagarol or sezamin, belongs to the class of organic compounds known as furanoid lignans. These are lignans with a structure that contains either a tetrahydrofuran ring, a furan ring, or a furofuan ring system, that arises from the joining of the two phenylpropanoid units. (+)-Sesamin is an extremely weak basic (essentially neutral) compound (based on its pKa). (+)-Sesamin is found, on average, in the highest concentration within sesames. (+)-Sesamin has also been detected, but not quantified in, several different foods, such as fats and oils, flaxseeds, ginkgo nuts, and ucuhuba. This could make (+)-sesamin a potential biomarker for the consumption of these foods.

Cytoplasm Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 13079-95-3
  • CAS Registry Number: 607-80-7
  • CAS Registry Number: 81602-22-4
  • PubChem: 5204
  • PubChem: 72307
  • ChEBI: ChEBI:66470
  • HMDB: HMDB0034256
  • HMDB: HMDB0242327
  • KEGG: C10882
  • BioCyc: CPD-8922
  • NCBI MeSH: sesamin
  • Wikipedia: Sesamin
  • RefMet: RM0187185
  • MoNA: VF-NPL-QEHF003808
  • MoNA: VF-NPL-QEHF003809
  • MoNA: VF-NPL-QEHF003810
  • MoNA: VF-NPL-QEHF003811
  • MoNA: VF-NPL-QEHF003812
  • MoNA: VF-NPL-QEHF003813
  • MoNA: VF-NPL-QEHF003814
  • MoNA: VF-NPL-QEHF003815
  • MoNA: VF-NPL-QEHF003816
  • MoNA: VF-NPL-QEHF003817
  • MoNA: VF-NPL-QEHF003818
  • MoNA: VF-NPL-QEHF003819
  • MoNA: VF-NPL-QEHF003820
  • MoNA: VF-NPL-QEHF003821
  • MoNA: VF-NPL-QEHF003822
  • Metlin: METLIN_63053
  • Coconut NaturalProduct: CNP0123354.12
  • Coconut NaturalProduct: CNP0123354.5

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R11955 2.1.5.1 (+)-sesamin:tetrahydrofolate N-methylenetransferase
KEGG:R12154 1.14.19.74 (+)-piperitol,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (cyclizing)
Rhea:RHEA:41012 2.1.5.1 (+)-sesamin + (6S)-5,6,7,8-tetrahydrofolyl-(γ-L-Glu)(n) => (+)-sesamin monocatechol + (6R)-5,10-methylenetetrahydrofolyl-(γ-L-Glu)(n)
Rhea:RHEA:41013 2.1.5.1 (+)-sesamin monocatechol + (6R)-5,10-methylenetetrahydrofolyl-(γ-L-Glu)(n) => (+)-sesamin + (6S)-5,6,7,8-tetrahydrofolyl-(γ-L-Glu)(n)
Rhea:RHEA:41014 2.1.5.1 (+)-sesamin + (6S)-5,6,7,8-tetrahydrofolyl-(γ-L-Glu)(n) <=> (+)-sesamin monocatechol + (6R)-5,10-methylenetetrahydrofolyl-(γ-L-Glu)(n)
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+
BioCyc:RXN-18465 2.1.5.1 CPD-8922 + THF-GLU-N --> CPD-19800 + METHYLENE-THF-GLU-N
BioCyc:RXN-13817 1.-.-.- sesamin hydroxylase
BioCyc:RXN-8696 1.14.19.74 CPD-8921 + Red-NADPH-Hemoprotein-Reductases + OXYGEN-MOLECULE --> CPD-8922 + Ox-NADPH-Hemoprotein-Reductases + 2 WATER
BioCyc:RXN-8705 1.-.-.- 2 CPD-8922 + OXYGEN-MOLECULE --> 2 CPD-8928
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Organism Source

Taxonomy Source

  1. Raulinoa echinata [ncbi taxid: 1331808]
  2. Acanthopanax divaricatus var.albeofructus C.S.YOOK et T.H.KIM [ncbi taxid: ]
  3. Acanthopanax gracilistylus [ncbi taxid: ]
  4. Acanthopanax sessiliflorum [ncbi taxid: ]
  5. Agathis lanceolata [ncbi taxid: 56989]
  6. Aglaia elaeagnoidea [ncbi taxid: 201007]
  7. Aglaia meridionalis [ncbi taxid: 306524]
  8. Alcyonium grandis [ncbi taxid: ]
  9. Allium ursinum [ncbi taxid: 4684]
  10. Ammi majus [ncbi taxid: 48026]
  11. Amycolatopsis lurida [ncbi taxid: 31959]
  12. Anacystis cyanea [ncbi taxid: ]
  13. Antrodia camphorata [ncbi taxid: ]
  14. Aplidium orthium [ncbi taxid: ]
  15. Apterostigma dentigerum [ncbi taxid: 257670]
  16. Arcangelisia gusanlung [ncbi taxid: 432629]
  17. Aristolochia elegans [ncbi taxid: 143780]
  18. Artemisia austriaca [ncbi taxid: 205362]
  19. Artemisia schmidtiana [ncbi taxid: 669138]
  20. Asarum heterotropoides [ncbi taxid: 366663]
  21. Asarum sieboldii [ncbi taxid: 76098]
  22. Asiasarum heterotropoides [ncbi taxid: ]
  23. Asiasarum sieboldii [ncbi taxid: ]
  24. Aspergillus candidus [ncbi taxid: 41067]
  25. Astragalus gummifer [ncbi taxid: 339493]
  26. Babylonia japonica [ncbi taxid: 167134]
  27. Beauveria felina [ncbi taxid: ]
  28. Brenneria rubrifaciens [ncbi taxid: 55213]
  29. Brickellia pendula [ncbi taxid: 1550857]
  30. Callyspongia truncata [ncbi taxid: ]
  31. Cardiospermum halicacabum [ncbi taxid: 289799]
  32. Centaurea nigrescens [ncbi taxid: 1308045]
  33. Chaetomium retardatum [ncbi taxid: ]
  34. Chamaemelum scariosum [ncbi taxid: 179397]
  35. Chrysolaena propinqua [ncbi taxid: 2067294]
  36. Cinnamomum camphora [ncbi taxid: 13429]
  37. Cinnamomum subavenium [ncbi taxid: 977953]
  38. Cirsium japonicum [ncbi taxid: 516546]
  39. Citrus tankan [ncbi taxid: 1008980]
  40. Cladiella krempfi [ncbi taxid: 1382565]
  41. Cladonia pseudodidyma [ncbi taxid: ]
  42. Cladosporium herbarum [ncbi taxid: 29918]
  43. Cleidion brevipetiolatum [ncbi taxid: 1679355]
  44. Coleus carnosus [ncbi taxid: ]
  45. Colubrina asiatica [ncbi taxid: 106664]
  46. Conyza canadensis [ncbi taxid: ]
  47. Copaifera paupera [ncbi taxid: 1954542]
  48. Coreopsis fasciculata [ncbi taxid: 1532913]
  49. Cortinarius basirubescens [ncbi taxid: 742017]
  50. Crepis foetida [ncbi taxid: 268017]
  51. Crinum defixum [ncbi taxid: 209091]
  52. Crotalaria lechnaultii [ncbi taxid: ]
  53. Cuphea carthagenensis [ncbi taxid: 312566]
  54. Cuscuta chinensis [ncbi taxid: 267557]
  55. Daphne blagayana [ncbi taxid: 653935]
  56. Daphne genkwa [ncbi taxid: 1477590]
  57. Digitalis obscura [ncbi taxid: 202408]
  58. Dioscoreophyllum cumminsii [ncbi taxid: 3457]
  59. Dipterocarpus pilosus [ncbi taxid: ]
  60. Dorstenia lindeniana [ncbi taxid: 984813]
  61. Dracaena concinna [ncbi taxid: 1280193]
  62. Dunaliella acidophila [ncbi taxid: 38272]
  63. Echinus miliaris [ncbi taxid: ]
  64. Eleutherococcus senticosus [ncbi taxid: 82096]
  65. Entandrophragma cylindricum [ncbi taxid: 179994]
  66. Erythrina orientalis [ncbi taxid: ]
  67. Escallonia philippiana [ncbi taxid: ]
  68. Eskemukerjea megacarpum [ncbi taxid: 154596]
  69. Euphorbia segetalis [ncbi taxid: 38847]
  70. Fagara heitzii [ncbi taxid: ]
  71. Ficus maxima [ncbi taxid: 100557]
  72. Garcinia hombroniana [ncbi taxid: 180107]
  73. Gleichenia glauca [ncbi taxid: ]
  74. Helipterum strictum [ncbi taxid: ]
  75. Hesperocyparis nevadensis [ncbi taxid: 48931]
  76. Hilliardiella oligocephala [ncbi taxid: 434668]
  77. Hippocratea indica [ncbi taxid: ]
  78. Isodon amethystoides [ncbi taxid: 662904]
  79. Juniperus thurifera [ncbi taxid: 177241]
  80. Lactobacillus acidophilus [ncbi taxid: 1579]
  81. Lathyrus macrorrhizus [ncbi taxid: ]
  82. Laurencia elata [ncbi taxid: ]
  83. Laurencia saitoi [ncbi taxid: 1583034]
  84. Lentinellus omphalodes [ncbi taxid: 5356]
  85. Leptospermum scoparium [ncbi taxid: 295139]
  86. Liparis keitaoensis [ncbi taxid: ]
  87. Lotus villosus [ncbi taxid: ]
  88. Lycoris x chejuensis [ncbi taxid: 1306909]
  89. Machaerium mucronulatum [ncbi taxid: ]
  90. Magnolia acuminata [ncbi taxid: 3404]
  91. Manduca sexta [ncbi taxid: 7130]
  92. Matteuccia struthiopteris [ncbi taxid: 3277]
  93. Mesua elegans [ncbi taxid: ]
  94. Michelia rajaniana [ncbi taxid: ]
  95. Millettia racemosa [ncbi taxid: ]
  96. Modiolus demissus [ncbi taxid: ]
  97. Moquiniastrum paniculatum [ncbi taxid: 1542361]
  98. Mosla scabra [ncbi taxid: 1898873]
  99. Neolitsea pulchella [ncbi taxid: 344115]
  100. Ochtodes crockeri [ncbi taxid: 508041]
  101. Onychopetalum amazonicum [ncbi taxid: 334814]
  102. Ophioglossum vulgatum [ncbi taxid: 49227]
  103. Ophiorrhiza kuroiwae [ncbi taxid: 367364]
  104. Orthosiphon wulfenioides [ncbi taxid: 662934]
  105. Oscillatoria princeps [ncbi taxid: 132603]
  106. Ozoroa insignis [ncbi taxid: 289735]
  107. Parastrephia lepidophylla [ncbi taxid: 382035]
  108. Parmelia conspersa [ncbi taxid: ]
  109. Penstemon secundiflorus [ncbi taxid: 388204]
  110. Phedimus kamtschaticus [ncbi taxid: 91120]
  111. Phlogacanthus thyrsiflorus [ncbi taxid: 526790]
  112. Phora atra [ncbi taxid: 92542]
  113. Phormia regina [ncbi taxid: 7380]
  114. Phytolacca acinosa [ncbi taxid: 3528]
  115. Piper arboreum [ncbi taxid: 130381]
  116. Piper longum [ncbi taxid: 49511]
  117. Piper retrofractum [ncbi taxid: 130414]
  118. Plumbago europaea [ncbi taxid: 114226]
  119. Podocarpus lawrencei [ncbi taxid: 120621]
  120. Polyporus sulphureus [ncbi taxid: ]
  121. Pouzolzia occidentalis [ncbi taxid: ]
  122. Pseudocyphellaria hirsuta [ncbi taxid: 534610]
  123. Punica granatum [ncbi taxid: 22663]
  124. Pyrocystis lunula [ncbi taxid: 2972]
  125. Russula subnigricans [ncbi taxid: 258989]
  126. Ruta microcarpa [ncbi taxid: 452792]
  127. Sarcomyxa serotina [ncbi taxid: 40488]
  128. Selinum carvifolium [ncbi taxid: ]
  129. Senecio erraticus [ncbi taxid: ]
  130. Sesamum indicum [ncbi taxid: 4182]
  131. Sesamum orientale [ncbi taxid: ]
  132. Sidastrum acuminatum [ncbi taxid: ]
  133. Simmondsia chinensis [ncbi taxid: 3999]
  134. Stevia serrata [ncbi taxid: 558511]
  135. Syncolostemon parviflorus [ncbi taxid: 231075]
  136. Tabebuia rosea [ncbi taxid: 429709]
  137. Taiwanofungus camphoratus [ncbi taxid: 2696576]
  138. Talaromyces wortmanni [ncbi taxid: ]
  139. Tanacetum santolina [ncbi taxid: 1115790]
  140. Thuja plicata [ncbi taxid: 3316]
  141. Timonius kaniensis [ncbi taxid: ]
  142. Triglochin maritima [ncbi taxid: 55501]
  143. Umbelopsis vinacea [ncbi taxid: 44442]
  144. Urtica triangularis [ncbi taxid: 1303701]
  145. Vernonia tufnellae [ncbi taxid: ]
  146. Vigna angularis [ncbi taxid: 3914]
  147. Xanthoxylum tingoassuiba [ncbi taxid: ]
  148. Zanthoxylum monophyllum [ncbi taxid: 43887]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5469 sesamin biosynthesis
BioCyc:META_PWY-7139 sesaminol glucoside biosynthesis
PlantCyc:SPENNELLII_PWY-7139 sesaminol glucoside 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:CGIGANTEA_PWY-7139 sesaminol glucoside 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:OEUROPAEA_SYLVESTRIS_PWY-7139 sesaminol glucoside biosynthesis
PlantCyc:OILSEEDRAPE_PWY-5469 sesamin biosynthesis
View All Pathways