(-)-α-Gurjunene (BioCAD00000000014)

microbial natural products plant natural products marine natural products

Metabolite Card

Chinese Name: (-)-alpha-古芸烯
Formula: C15H24 (204.1878)
SMILES: 

C[C@@H]1CC[C@@H]2[C@H](C3=C(C)CC[C@H]13)C2(C)C

Synonyms [en]

(-)-alpha-Gurjunene; Gurjunene-alpha; alpha-Gurjunene; Isoledene; (1aR,4R,4aR,7bS)-1,1,4,7-tetramethyl-1a,2,3,4,4a,5,6,7b-octahydro-1H-cyclopropa[e]azulene; 95910-36-4

Reviewed

Last reviewed on 2026-04-16.

Cite this Page

(-)-α-Gurjunene. 数据之源，洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/α-Gurjunene (retrieved 2026-08-20) (CAD Registry RN: BioCAD00000000014). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Alpha-Gurjunene or (-)-Alpha-Gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid as it synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Gurjunene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a colorless clear Liquid and has a woody, balsamic odor. It is used as a perfuming agent. Alpha-gurjunene is found in many plants, essential oils and foods including allspice, bay leaf, carrot seeds, eucalyptus, guava, parsley, black papper, sage and tea tree oil.

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 111-71-7
  • CAS Registry Number: 1181210-01-4
  • CAS Registry Number: 489-40-7
  • CAS Registry Number: 95910-36-4
  • PubChem: 133110026
  • PubChem: 15431199
  • PubChem: 15560276
  • PubChem: 521243
  • PubChem: 530426
  • ChEBI: ChEBI:61699
  • HMDB: HMDB0036417
  • HMDB: HMDB0304686
  • KEGG: C19734
  • BioCyc: CPD-12891
  • RefMet: RM0160282
  • MoNA: JP002836
  • Metlin: METLIN_73325
  • Coconut NaturalProduct: CNP0128955.1
  • Coconut NaturalProduct: CNP0128955.3
  • Coconut NaturalProduct: CNP0256345.1
  • Coconut NaturalProduct: CNP0256345.2
  • PMHub: MS000027393
  • PMHub: MS000089954
  • metaboanalyst: da5dc46e60530c40dcb7a8ef97ba3994
  • HERB: HBIN011333
  • HERB: HBIN015535
  • HERB: HBIN029055
  • HERB: HBIN030861
  • HERB: HBIN030862
  • HERB: HBIN042101

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R09606 4.2.3.72 (2E,6E)-farnesyl-diphosphate diphosphate-lyase [(-)-alpha-gurjunene-forming]
Rhea:RHEA:29508 4.2.3.72 (2E,6E)-farnesyl diphosphate => (−)-α-gurjunene + diphosphate
Rhea:RHEA:29509 4.2.3.72 (−)-α-gurjunene + diphosphate => (2E,6E)-farnesyl diphosphate
Rhea:RHEA:29510 4.2.3.72 (2E,6E)-farnesyl diphosphate <=> (−)-α-gurjunene + diphosphate
BioCyc:RXN-11910 4.2.3.72 FARNESYL-PP --> CPD-12891 + PPI
Rhea:RHEA:29507 [29507] (2E,6E)-farnesyl diphosphate = (-)-alpha-gurjunene + diphosphate
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Mass Spectrum
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View All Mass Spectrum
Organism Source

Taxonomy Source

  1. Alstonia muelleriana [ncbi taxid: 1382056]
  2. Amphimedon terpenensis [ncbi taxid: ]
  3. Angelica dahurica [ncbi taxid: 48101]
  4. Annona reticulata [ncbi taxid: 301862]
  5. Anthyllis hermanniae [ncbi taxid: 181246]
  6. Artemisia cina [ncbi taxid: 1473222]
  7. Ascocoryne sarcoides [ncbi taxid: 139061]
  8. Astilbe odontophylla [ncbi taxid: 1277852]
  9. Balsamum tolutanum [ncbi taxid: ]
  10. Barbarea vulgaris subsp. arcuata [ncbi taxid: 767412]
  11. Cistus creticus [ncbi taxid: 191224]
  12. Clerodendrum brachyanthum [ncbi taxid: ]
  13. Coreopsis nodosa [ncbi taxid: ]
  14. Cryptocarya triplinervis [ncbi taxid: 136115]
  15. Cynanchum sibiricum [ncbi taxid: 2171542]
  16. Cyperus rotundus L. [ncbi taxid: ]
  17. Dacrydium cupressinum [ncbi taxid: 56890]
  18. Daucus carota [ncbi taxid: 4039]
  19. Diospyros heterotricha [ncbi taxid: ]
  20. Dipterocarpus dyeri [ncbi taxid: 340441]
  21. Elaeocarpus dolichostylus [ncbi taxid: 2501685]
  22. Euphorbia officinarum subsp. echinus [ncbi taxid: 1129987]
  23. Glycine tomentella [ncbi taxid: 44015]
  24. Guarea macrophylla ssp.tuberculata [ncbi taxid: ]
  25. Haematococcus lacustris [ncbi taxid: 44745]
  26. Hydnocarpus venenata [ncbi taxid: ]
  27. Hypoestes phyllostachya [ncbi taxid: 101678]
  28. Hypoxylon rubiginosum [ncbi taxid: 110542]
  29. Kaempferia galanga [ncbi taxid: 97750]
  30. Lamna ditropis [ncbi taxid: 38578]
  31. Lecanora rupicola [ncbi taxid: ]
  32. Leptospermum scoparium [ncbi taxid: 295139]
  33. Lilium medeoloides [ncbi taxid: 79006]
  34. Limonia crenulata [ncbi taxid: ]
  35. Lycopodium casuarinoides [ncbi taxid: ]
  36. Macleaya cordata [ncbi taxid: 56857]
  37. Melaleuca leucadendra [ncbi taxid: 164936]
  38. Menyanthes trifoliata [ncbi taxid: 28525]
  39. Mycale cecilia [ncbi taxid: 1325603]
  40. Nicotiana undulata [ncbi taxid: 118713]
  41. Panax ginseng [ncbi taxid: 4054]
  42. Panax notoginseng [ncbi taxid: 44586]
  43. Panax schinseng [ncbi taxid: ]
  44. Parmelia barbata [ncbi taxid: ]
  45. Passiflora incarnata [ncbi taxid: 159425]
  46. Piper arboreum [ncbi taxid: 130381]
  47. Piper fimbriulatum [ncbi taxid: 425151]
  48. Piper obliquum [ncbi taxid: 425162]
  49. Piptocarpha chontalensis [ncbi taxid: ]
  50. Pogostemon cablin [ncbi taxid: 28511]
  51. Pterocladiella tenuis [ncbi taxid: 947988]
  52. Rhaponticum carthamoides [ncbi taxid: ]
  53. Roccella tinctoria [ncbi taxid: 269078]
  54. Saccharomyces pastori [ncbi taxid: ]
  55. Sambucus nigra [ncbi taxid: 4202]
  56. Senecio paludaffinis [ncbi taxid: 1892289]
  57. Senegalia tenuifolia [ncbi taxid: 1130855]
  58. Solanum lycopersicum [ncbi taxid: 4081]
  59. Streptomyces flocculus [ncbi taxid: ]
  60. Streptomyces sp. strain GWS-BW-H5 [ncbi taxid: ]
  61. Tachigalia paniculata [ncbi taxid: ]
  62. Tersonia brevipes [ncbi taxid: 415847]
  63. Thermotoga maritima [ncbi taxid: 2336]
  64. Toona ciliata [ncbi taxid: 67918]
  65. Trigonella grandiflora [ncbi taxid: 1210110]
  66. Tripolium pannonicum [ncbi taxid: 74787]
  67. Usnea magellanica [ncbi taxid: ]
  68. Uvaria calamistrata [ncbi taxid: 672966]
  69. Uvaria chamae [ncbi taxid: 174970]
  70. Artemisia capillaries [ncbi taxid: ]
  71. Cyperus rotundus [ncbi taxid: 512623]
  72. Houttuynia cordata [ncbi taxid: 16752]
  73. Ligusticum chuanxiong [ncbi taxid: 2689076]
  74. Thymus broussonetti [ncbi taxid: ]
  75. Acorus gramineus [ncbi taxid: 55184]
  76. Acorus tatarinowii [ncbi taxid: 123564]
  77. Agastache rugosa [ncbi taxid: 39271]
  78. Angelica acutiloba [ncbi taxid: 55605]
  79. Angelica gigas [ncbi taxid: 85712]
  80. Angelica sinensis [ncbi taxid: 165353]
  81. Artemisia capillaris [ncbi taxid: 265783]
  82. Asarum heterotropoides [ncbi taxid: 366663]
  83. Asarum sieboldii [ncbi taxid: 76098]
  84. Asiasarum heterotropoides [ncbi taxid: ]
  85. Asiasarum sieboldii [ncbi taxid: ]
  86. Atractylodes lancea [ncbi taxid: 41486]
  87. Atractylodes macrocephala [ncbi taxid: 265785]
  88. Bupleurum chinense [ncbi taxid: 52451]
  89. Bupleurum falcatum [ncbi taxid: 46367]
  90. Bupleurum scorzonerifolium [ncbi taxid: 48105]
  91. Chrysanthemum indicum [ncbi taxid: 146995]
  92. Chrysanthemum x morifolium [ncbi taxid: 41568]
  93. Citrus maxima [ncbi taxid: 37334]
  94. Citrus reticulata [ncbi taxid: 85571]
  95. Citrus unshiu [ncbi taxid: 55188]
  96. Lepidozia fauriana [ncbi taxid: 989928]
  97. Melaleuca alternifolia [ncbi taxid: 164405]
  98. Schisandra chinensis [ncbi taxid: 50507]
  99. Scutellaria barbata [ncbi taxid: 396367]
  100. Solanum lycopersicum [ncbi taxid: 4081]
  101. Tritomaria quinquedentata (Huds.) [ncbi taxid: ]
  102. Acorus gramineus [ncbi taxid: 55184]
  103. Acorus tatarinowii [ncbi taxid: 123564]
  104. Agastache rugosa [ncbi taxid: 39271]
  105. Angelica acutiloba [ncbi taxid: 55605]
  106. Angelica gigas [ncbi taxid: 85712]
  107. Angelica sinensis [ncbi taxid: 165353]
  108. Artemisia capillaris [ncbi taxid: 265783]
  109. Asarum heterotropoides [ncbi taxid: 366663]
  110. Asarum sieboldii [ncbi taxid: 76098]
  111. Asiasarum heterotropoides [ncbi taxid: ]
  112. Asiasarum sieboldii [ncbi taxid: ]
  113. Atractylodes lancea [ncbi taxid: 41486]
  114. Atractylodes macrocephala [ncbi taxid: 265785]
  115. Bupleurum chinense [ncbi taxid: 52451]
  116. Bupleurum falcatum [ncbi taxid: 46367]
  117. Bupleurum scorzonerifolium [ncbi taxid: 48105]
  118. Chrysanthemum indicum [ncbi taxid: 146995]
  119. Chrysanthemum x morifolium [ncbi taxid: 41568]
  120. Citrus maxima [ncbi taxid: 37334]
  121. Citrus reticulata [ncbi taxid: 85571]
  122. Citrus unshiu [ncbi taxid: 55188]
  123. Schisandra chinensis [ncbi taxid: 50507]
  124. Scutellaria barbata [ncbi taxid: 396367]

Pathway Synthetic

pathway id name
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