Farnesol (BioCAD00000020330)

blood epidermis fibroblasts intestine kidney plant natural products microbial natural products

Metabolite Card

Formula: C15H26O (222.1984)
SMILES: CC(C)=CCC\C(C)=C\CC\C(C)=C\CO

Synonyms [en]

FARNESOL; Nikkosome; Farnesyl alcohol; trans-Farnesol; 10-dodecatrien-12-ol; 2,6-Di-trans-farnesol

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Farnesol. 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: BioCAD00000020330). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Farnesol is a signaling molecule that is derived from farnesyl diphosphate, an intermediate in the isoprenoid/cholesterol biosynthetic pathway. Farnesol is a 15 carbon isoprenoid alcohol is the corresponding dephosphorylated form of the isoprenoid farnesyl diphosphate. Farnesol has a potential role in controlling the degradation of 3-hydroxy-3-methylglutaryl coenzyme A (HMGCoA) reductase (EC 1.1.1.34, NADPH-hydroxymethylglutaryl-CoA reductase). The enzyme is stabilized under conditions of cellular sterol depletion (e.g. statin-treated cells) and rapidly degraded in sterol-loaded cells. In mammalian cells, this enhanced degradation is dependent on the presence of both a sterol and a non-sterol derived from the isoprenoid pathway; farnesol, the dephosphorylated form of farnesyl diphosphate, can function as the non-sterol component. Farnesol has been shown to activate the farnesoid receptor (FXR), a nuclear receptor that forms a functional heterodimer with RXR. Thus, dephosphorylation of farnesyl diphosphate, an intermediate in the cholesterol synthetic pathway, might produce an active ligand for the FXR:RXR heterodimer. The physiological ligand for FXR remains to be identified; farnesol, may simply mimic the unidentified natural ligand(s). In addition, exogenous farnesol have an effect on several other physiological processes, including inhibition of phosphatidylcholine biosynthesis, induction of apoptosis, inhibition of cell cycle progression and actin cytoskeletal disorganization. Farnesol cellular availability is an important determinant of vascular tone in animals and humans, and provides a basis for exploring farnesyl metabolism in humans with compromised vascular function as well as for using farnesyl analogues as regulators of arterial tone in vivo. A possible metabolic fate for farnesol is its conversion to farnesoic acid, and then to farnesol-derived dicarboxylic acids (FDDCAs) which would then be excreted in the urine. Farnesol can also be oxidized to a prenyl aldehyde, presumably by an alcohol dehydrogenase (ADH), and that this activity resides in the mitochondrial and peroxisomal. Liver Endoplasmic reticulum and peroxisomal fractions are able to phosphorylate farnesol to Farnesyl diphosphate in a Cytosine triphosphate dependent fashion. (PMID: 9812197, 8636420, 9083051, 9015362). Prenol is polymerized by dehydration reactions; when there are at least four isoprene units (n in the above formula is greater than or equal to four), the polymer is called a polyprenol. Polyprenols can contain up to 100 isoprene units (n=100) linked end to end with the hydroxyl group (-OH) remaining at the end. These isoprenoid alcohols are also called terpenols These isoprenoid alcohols are important in the acylation of proteins, carotenoids, and fat-soluble vitamins A, E and K. They are also building blocks for plant oils such as farnesol and geraniol. Prenol is also a building block of cholesterol (built from six isoprene units), and thus of all steroids. Prenol has sedative properities, it is probably GABA receptor allosteric modulator.When the isoprene unit attached to the alcohol is saturated, the compound is referred to as a dolichol. Dolichols are important as glycosyl carriers in the synthesis of polysaccharides.(Wikipedia).

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 4602-84-0
  • PubChem: 1549107
  • PubChem: 445070
  • ChEBI: ChEBI:16619
  • HMDB: HMDB0004305
  • KEGG: C06081
  • Wikipedia: Farnesol
  • MoNA: Bruker_HCD_library001844
  • MoNA: FiehnLib000508
  • MoNA: FiehnLib000509
  • MoNA: FiehnLib000510
  • MoNA: HMDB0004305_c_ms_1424
  • MoNA: HMDB0004305_c_ms_1437
  • MoNA: HMDB0004305_c_ms_1473
  • MoNA: VF-NPL-LTQ006151
  • MoNA: VF-NPL-LTQ006152
  • MoNA: VF-NPL-QEHF002935
  • MoNA: VF-NPL-QEHF002936
  • MoNA: VF-NPL-QEHF002937
  • Coconut NaturalProduct: CNP0232612.0

Class / Ontology

Metabolic Network
ID EC Number Name
View More
Organism Source

Taxonomy Source

  1. Abelmoschus moschatus [ncbi taxid: 1170222]
  2. Acacia aulacocarpa [ncbi taxid: 138511]
  3. Aceriphyllum rossii [ncbi taxid: ]
  4. Acrocarpia paniculata [ncbi taxid: 717668]
  5. Agnorhiza bolanderi [ncbi taxid: 230216]
  6. Alligator mississippiensis [ncbi taxid: 8496]
  7. Alpinia katsumadai [ncbi taxid: ]
  8. Anaxagorea clavata [ncbi taxid: ]
  9. Anemone flaccida [ncbi taxid: ]
  10. Anodendron affine [ncbi taxid: 582712]
  11. Apis mellifera [ncbi taxid: 7460]
  12. Araujia sericifera [ncbi taxid: 63463]
  13. Ardisia neriifolia [ncbi taxid: 2184479]
  14. Aria pallescens [ncbi taxid: ]
  15. Arnica nevadensis [ncbi taxid: 436208]
  16. Artemisia capillaris [ncbi taxid: 265783]
  17. Artemisia monogyna [ncbi taxid: 1903222]
  18. Aspidosperma subincanum [ncbi taxid: 2743209]
  19. Bassia butyracea [ncbi taxid: ]
  20. Beyeria brevifolia [ncbi taxid: 2752376]
  21. Bursaria spinosa [ncbi taxid: 105281]
  22. Callistemon polandii [ncbi taxid: 73732]
  23. Candida albicans [ncbi taxid: 5476]
  24. Cedrela salvadorensis [ncbi taxid: 582829]
  25. Centella asiatica [ncbi taxid: 48106]
  26. Chamaecyparis lawsoniana (A. Murray bis) Parl. [ncbi taxid: ]
  27. Chimonanthus fragrans [ncbi taxid: ]
  28. Chloranthus tianmushanensis [ncbi taxid: ]
  29. Chromolaena odorata [ncbi taxid: 103745]
  30. Chromolaena pulchella [ncbi taxid: ]
  31. Chrysanthemum indicum [ncbi taxid: 146995]
  32. Chrysanthemum x morifolium [ncbi taxid: 41568]
  33. Cinnamomum verum [ncbi taxid: 128608]
  34. Citrullus lanatus [ncbi taxid: 3654]
  35. Citrus aurantium [ncbi taxid: ]
  36. Citrus aurantium var. amara engl. [ncbi taxid: ]
  37. Citrus maxima [ncbi taxid: 37334]
  38. Citrus reticulata [ncbi taxid: 85571]
  39. Cladonia evansii [ncbi taxid: 197026]
  40. Clathria basilana [ncbi taxid: ]
  41. Clonostachys rosea [ncbi taxid: 29856]
  42. Coccus fagi [ncbi taxid: ]
  43. Conocephalum conicum [ncbi taxid: 41839]
  44. Cryptocarya aschersoniana [ncbi taxid: 1345236]
  45. Cuminum cyminum [ncbi taxid: 52462]
  46. Curcuma longa [ncbi taxid: 136217]
  47. Cyclosorus esquirolii [ncbi taxid: ]
  48. Cymbopogon schoenanthus [ncbi taxid: 79841]
  49. Dendrosenecio kilimanjari [ncbi taxid: 109559]
  50. Descurainia sophia [ncbi taxid: 89411]
  51. Dipterocarpus alatus [ncbi taxid: 340438]
  52. Dolomiaea souliei [ncbi taxid: 454324]
  53. Drosera peltata [ncbi taxid: 4369]
  54. Echinops amplexicaulis [ncbi taxid: 910522]
  55. Elettaria cardamomum [ncbi taxid: 105181]
  56. Elsholtzia ciliata [ncbi taxid: 662901]
  57. Epaltes gariepina [ncbi taxid: 1548596]
  58. Eriobotrya japonica [ncbi taxid: 32224]
  59. Eucalyptus acaciiformis [ncbi taxid: 1711126]
  60. Eucalyptus camaldulensis [ncbi taxid: 34316]
  61. Eucalyptus citriodora [ncbi taxid: ]
  62. Eucalyptus socialis [ncbi taxid: 1711534]
  63. Eucarya spicata [ncbi taxid: ]
  64. Eucommia ulmoides [ncbi taxid: 4392]
  65. Eupatorium argentinum [ncbi taxid: ]
  66. Ficus formosana [ncbi taxid: 1127366]
  67. Fusarium gibbosum [ncbi taxid: 2126134]
  68. Garcinia cambogia [ncbi taxid: ]
  69. Gardenia fosbergii [ncbi taxid: ]
  70. Ginkgo biloba [ncbi taxid: 3311]
  71. Guatteria boliviana [ncbi taxid: 343271]
  72. Hertia cheirifolia [ncbi taxid: 430993]
  73. Hibiscus abelmoschus [ncbi taxid: ]
  74. Homo sapiens [ncbi taxid: 9606]
  75. Ilex affinis [ncbi taxid: 185489]
  76. Isodon kameba [ncbi taxid: ]
  77. Juniperus brevifolia [ncbi taxid: 746017]
  78. Kaempferia pulchra [ncbi taxid: 199647]
  79. Lactarius scrobiculatus [ncbi taxid: 93011]
  80. Licaria chrysophylla [ncbi taxid: 597316]
  81. Lindera aggregata [ncbi taxid: 545644]
  82. Lindera strichnifolia [ncbi taxid: ]
  83. Lobophytum depressum [ncbi taxid: 2486328]
  84. Lonicera japonica [ncbi taxid: 105884]
  85. Melaleuca cajuputi [ncbi taxid: 109355]
  86. Mentha arvensis [ncbi taxid: 292239]
  87. Mentha canadensis [ncbi taxid: 294733]
  88. Mosla chinensis [ncbi taxid: 516065]
  89. Nelumbo nucifera [ncbi taxid: 4432]
  90. Neolentinus lepideus [ncbi taxid: 38799]
  91. Nicotiana alata [ncbi taxid: 4087]
  92. Odixia angusta [ncbi taxid: 125740]
  93. Oenothera biennis [ncbi taxid: 3942]
  94. Origanum onites [ncbi taxid: 452416]
  95. Ormosia hosiei [ncbi taxid: 1642859]
  96. Ornithoglossum viride [ncbi taxid: 225807]
  97. Panax ginseng [ncbi taxid: 4054]
  98. Peritassa compta [ncbi taxid: ]
  99. Pertusaria truncata [ncbi taxid: ]
  100. Petasites laevigatus [ncbi taxid: ]
  101. Pheidole pallidula [ncbi taxid: 190770]
  102. Pittosporum undulatum [ncbi taxid: 23131]
  103. Pocillopora eydouxi [ncbi taxid: ]
  104. Polypodium decumanum [ncbi taxid: ]
  105. Prosopis glandulosa [ncbi taxid: ]
  106. Prunus laurocerasus [ncbi taxid: 32242]
  107. Pseudopterogorgia kallos [ncbi taxid: ]
  108. Psiadia dentata [ncbi taxid: 1225829]
  109. Pteris prolifera [ncbi taxid: ]
  110. Pterocarpus grandiflorus [ncbi taxid: ]
  111. Pyrosoma giganteum [ncbi taxid: ]
  112. Quercus aegilops [ncbi taxid: ]
  113. Rheedia acuminata [ncbi taxid: ]
  114. Rhizobium phaseoli [ncbi taxid: 396]
  115. Rubia tetragona [ncbi taxid: ]
  116. Salvia officinalis [ncbi taxid: 38868]
  117. Salvia thymoides [ncbi taxid: 392697]
  118. Santalum spicatum [ncbi taxid: 453088]
  119. Schisandra chinensis [ncbi taxid: 50507]
  120. Schizanthus tricolor [ncbi taxid: 360636]
  121. Scolymus hispanicus [ncbi taxid: 114287]
  122. Securidaca inappendiculata [ncbi taxid: 3091905]
  123. Senecio squalidus [ncbi taxid: 121554]
  124. Seriphidium cinum [ncbi taxid: ]
  125. Sesbania punicea [ncbi taxid: 543741]
  126. Simira eliezeriana [ncbi taxid: ]
  127. Sphaeranthus confertifolius [ncbi taxid: ]
  128. Stenostomum lucidum [ncbi taxid: 43446]
  129. Stigmatella aurantiaca DW4/3-1 [ncbi taxid: 378806]
  130. Streptomyces althioticus [ncbi taxid: 83380]
  131. Symphyocladia latiuscula [ncbi taxid: 396806]
  132. Taxodium mucronatum [ncbi taxid: 99812]
  133. Tephrosia purpurea [ncbi taxid: 228354]
  134. Torreya nucifera [ncbi taxid: 50189]
  135. Vaccinium corymbosum [ncbi taxid: 69266]
  136. Vitex madiensis [ncbi taxid: 1899206]
  137. Zea mays [ncbi taxid: 4577]
  138. Zingiber officinale [ncbi taxid: 94328]

Pathway Synthetic

pathway id name
View All Pathways