(-)-Menthone (BioCAD00000000072)

plant natural products microbial natural products

Metabolite Card

Formula: C10H18O (154.1358)
SMILES: CC(C)[C@@H]1CC[C@@H](C)CC1=O

Synonyms [en]

(-)-Menthone; l-MENTHONE; p-Menthan-3-one; (1R,4S)-p-menthan-3-one; (2S,5R)-2-isopropyl-5-methylcyclohexanone; (2S,5R)-5-methyl-2-(1-methylethyl)cyclohexanone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

(-)-Menthone. 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: BioCAD00000000072). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

(-)-Menthone, also known as (1R,4S)-menthone or L-menthone, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. (-)-Menthone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (-)-menthone is considered to be an isoprenoid lipid molecule.

Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 10276-21-8
  • CAS Registry Number: 10458-14-7
  • CAS Registry Number: 1074-95-9
  • CAS Registry Number: 132203-71-5
  • CAS Registry Number: 14073-97-3
  • CAS Registry Number: 15358-91-5
  • CAS Registry Number: 18675-34-8
  • CAS Registry Number: 20549-48-8
  • CAS Registry Number: 51773-45-6
  • CAS Registry Number: 53369-17-8
  • CAS Registry Number: 53538-30-0
  • CAS Registry Number: 61203-82-5
  • CAS Registry Number: 73348-34-2
  • CAS Registry Number: 89-80-5
  • PubChem: 26447
  • PubChem: 443159
  • ChEBI: ChEBI:15410
  • ChEBI: ChEBI:36503
  • HMDB: HMDB0035162
  • HMDB: HMDB0035783
  • LipidMaps: LMPR0102090004
  • KEGG: C00843
  • BioCyc: CPD-1909
  • NCBI MeSH: menthone
  • Wikipedia: Menthone
  • DrugBank: DB15920
  • RefMet: RM0046760
  • MoNA: HMDB0035162_c_ms_101716
  • MoNA: HMDB0035162_c_ms_101717
  • MoNA: HMDB0035162_c_ms_101718
  • MoNA: HMDB0035162_c_ms_102737
  • MoNA: HMDB0035162_c_ms_102738
  • MoNA: JP004932
  • MoNA: JP007382
  • Metlin: METLIN_41066
  • Coconut NaturalProduct: CNP0076060.0
  • Coconut NaturalProduct: CNP0086275.0
  • Coconut NaturalProduct: CNP0100257.2
  • Coconut NaturalProduct: CNP0177049.1
  • Coconut NaturalProduct: CNP0177049.3
  • Coconut NaturalProduct: CNP0177049.4
  • Coconut NaturalProduct: CNP0184664.2
  • Coconut NaturalProduct: CNP0219935.1
  • Coconut NaturalProduct: CNP0231491.1
  • Coconut NaturalProduct: CNP0288647.1
  • Coconut NaturalProduct: CNP0300873.0
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  • Coconut NaturalProduct: CNP0390712.6
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  • Coconut NaturalProduct: CNP0570744.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R02177 1.1.1.207 (-)-menthol:NADP+ oxidoreductase
KEGG:R02548 1.1.1.208 (+)-neomenthol:NADP+ oxidoreductase
KEGG:R06419 1.3.1.81 (-)-menthone:NADP+ oxidoreductase
KEGG:R08925 1.14.13.105 (-)-menthone,NADPH:oxygen oxidoreductase
Rhea:RHEA:13918 1.1.1.207 (−)-menthol + NADP+ => (1R,4S)-menthone + NADPH + H+
Rhea:RHEA:13919 1.1.1.207 (1R,4S)-menthone + NADPH + H+ => (−)-menthol + NADP+
Rhea:RHEA:13920 1.1.1.207 (−)-menthol + NADP+ <=> (1R,4S)-menthone + NADPH + H+
Rhea:RHEA:23813 1.1.1.208 (+)-neomenthol + NADP+ => (1R,4S)-menthone + NADPH + H+
Rhea:RHEA:23814 1.1.1.208 (1R,4S)-menthone + NADPH + H+ => (+)-neomenthol + NADP+
Rhea:RHEA:23815 1.1.1.208 (+)-neomenthol + NADP+ <=> (1R,4S)-menthone + NADPH + H+
Rhea:RHEA:25642 1.3.1.81 (1R,4S)-menthone + NADP+ => (R)-pulegone + NADPH + H+
Rhea:RHEA:25643 1.3.1.81 (R)-pulegone + NADPH + H+ => (1R,4S)-menthone + NADP+
Rhea:RHEA:25644 1.3.1.81 (1R,4S)-menthone + NADP+ <=> (R)-pulegone + NADPH + H+
Rhea:RHEA:32432 1.14.13.105 (1R,4S)-menthone + NADPH + O2 + H+ => (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O
Rhea:RHEA:32433 1.14.13.105 (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O => (1R,4S)-menthone + NADPH + O2 + H+
Rhea:RHEA:32434 1.14.13.105 (1R,4S)-menthone + NADPH + O2 + H+ <=> (4R,7S)-7-isopropyl-4-methyloxepan-2-one + NADP+ + H2O
BioCyc:RXN-5163 1.3.1.81 CPD-4942 + NADPH + PROTON --> CPD-1909 + NADP
BioCyc:--MENTHOL-DEHYDROGENASE-RXN 1.1.1.207 PROTON + CPD-1909 + NADPH --> NADP + --MENTHOL
BioCyc:RXN-9441 1.14.13.105 CPD-1909 + NADPH + PROTON + OXYGEN-MOLECULE --> CPD-10107 + NADP + WATER
BioCyc:+-NEOMENTHOL-DEHYDROGENASE-RXN 1.1.1.208 PROTON + NADPH + CPD-1909 --> NADP + CPD-1905
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Organism Source

Taxonomy Source

  1. Cephalotaxus fortunei [ncbi taxid: 66169]
  2. Artemisia argyi [ncbi taxid: 259893]
  3. Artemisia capillaris [ncbi taxid: 265783]
  4. Artemisia montana [ncbi taxid: 669134]
  5. Artemisia princeps [ncbi taxid: 223870]
  6. Daucus carota [ncbi taxid: 4039]
  7. Zanthoxylum bungeanum [ncbi taxid: 328401]
  8. Zanthoxylum piperitum [ncbi taxid: 354529]
  9. Zanthoxylum schinifolium [ncbi taxid: 354530]
  10. Artemisia argyi [ncbi taxid: 259893]
  11. Artemisia capillaris [ncbi taxid: 265783]
  12. Artemisia montana [ncbi taxid: 669134]
  13. Artemisia princeps [ncbi taxid: 223870]
  14. Daucus carota [ncbi taxid: 4039]
  15. Zanthoxylum bungeanum [ncbi taxid: 328401]
  16. Zanthoxylum piperitum [ncbi taxid: 354529]
  17. Zanthoxylum schinifolium [ncbi taxid: 354530]
  18. Pinus sylvestris [ncbi taxid: 3349]
  19. Aconitum leucostomum [ncbi taxid: 632164]
  20. Actaea dahurica [ncbi taxid: 64029]
  21. Actaea heracleifolia [ncbi taxid: 64034]
  22. Actaea simplex [ncbi taxid: 64042]
  23. Akebia quinata [ncbi taxid: 13331]
  24. Akebia trifoliata [ncbi taxid: 155132]
  25. Alpinia katsumadai [ncbi taxid: ]
  26. Anarsia lineatella [ncbi taxid: 1101080]
  27. Apollonias barbujana [ncbi taxid: ]
  28. Aquilegia ecalcarata [ncbi taxid: 46965]
  29. Artemisia argyi [ncbi taxid: 259893]
  30. Artemisia hanseniana [ncbi taxid: ]
  31. Artemisia montana [ncbi taxid: 669134]
  32. Artemisia princeps [ncbi taxid: 223870]
  33. Atractylodes lancea [ncbi taxid: 41486]
  34. Atractylodes macrocephala [ncbi taxid: 265785]
  35. Blumea mollis [ncbi taxid: 119169]
  36. Ceanothus velutinus [ncbi taxid: 54785]
  37. Chlorophytum borivilianum [ncbi taxid: 503355]
  38. Cimicifuga foetida [ncbi taxid: ]
  39. Dipterocarpus dyeri [ncbi taxid: 340441]
  40. Echinops grijsii [ncbi taxid: 1804979]
  41. Elsholtzia splendens [ncbi taxid: 475396]
  42. Eucalyptus viminalis [ncbi taxid: 155764]
  43. Fragaria vesca [ncbi taxid: 57918]
  44. Garcinia scortechinii [ncbi taxid: 180116]
  45. Gardenia tubifera [ncbi taxid: 1240870]
  46. Herba glechomae longitubae [ncbi taxid: ]
  47. Hypericum perforatum [ncbi taxid: 65561]
  48. Inula helenium [ncbi taxid: 55635]
  49. Ipomoea cairica [ncbi taxid: 129201]
  50. Isodon lophanthoides [ncbi taxid: 204133]
  51. Kopsia grandifolia [ncbi taxid: 1750995]
  52. Lasianthus fordii [ncbi taxid: 1406743]
  53. Ledebouria socialis [ncbi taxid: 34191]
  54. Leonurus heterophyllus [ncbi taxid: ]
  55. Ligusticum jeholense [ncbi taxid: 49553]
  56. Ligusticum sinense [ncbi taxid: ]
  57. Ligusticum tenuissimum [ncbi taxid: ]
  58. Lycopus europaeus [ncbi taxid: 260603]
  59. Mentha aquatica [ncbi taxid: 190902]
  60. Mentha arvensis [ncbi taxid: 292239]
  61. Mentha canadensis [ncbi taxid: 294733]
  62. Mentha gattefosse [ncbi taxid: ]
  63. Mentha haplocalyx [ncbi taxid: ]
  64. Mentha piperita [ncbi taxid: ]
  65. Mentha piperita L. [ncbi taxid: ]
  66. Mentha pulegium [ncbi taxid: 294739]
  67. Mentha sp. [ncbi taxid: 3133031]
  68. Mentha spicata [ncbi taxid: 29719]
  69. Mentha spp. [ncbi taxid: ]
  70. Mentha x piperita [ncbi taxid: 34256]
  71. Mentha x piperita L. [ncbi taxid: ]
  72. Ocimum basilicum [ncbi taxid: 39350]
  73. Panax innovans [ncbi taxid: ]
  74. Penicillium cinerascens [ncbi taxid: 70096]
  75. Perilla frutescens [ncbi taxid: 48386]
  76. Perilla frutescens var. acuta [ncbi taxid: 279737]
  77. Perilla frutescens var. arguta [ncbi taxid: 381201]
  78. Persea mexicana [ncbi taxid: ]
  79. Pinellia ternata [ncbi taxid: 199225]
  80. Pinus palustris [ncbi taxid: 46836]
  81. Rhaponticum uniflorum [ncbi taxid: ]
  82. Rhodobacter sphaeroides [ncbi taxid: ]
  83. Saussurea lappa [ncbi taxid: ]
  84. Schizonepeta tenuifolia [ncbi taxid: 2849020]
  85. Schizonepeta tenuisfolia [ncbi taxid: ]
  86. Scutellaria barbata [ncbi taxid: 396367]
  87. Senna alexandrina [ncbi taxid: 72402]
  88. Sordaria araneosa [ncbi taxid: 573841]
  89. Thymus quinquecostatus [ncbi taxid: 228974]
  90. Thymus vulgaris [ncbi taxid: 49992]
  91. Vitex negundo [ncbi taxid: 361442]
  92. Crocus sativus [ncbi taxid: 82528]
  93. Houttuynia cordata [ncbi taxid: 16752]
  94. Houttuynia emeiensis [ncbi taxid: ]
  95. Mentha spicata [ncbi taxid: 29719]
  96. Perilla frutescens var. arguta [ncbi taxid: 381201]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-3061 menthol biosynthesis
PlantCyc:PLANT_PWY-3061 menthol biosynthesis
PlantCyc:REDSAGE_PWY-3061 menthol biosynthesis
PlantCyc:ROSEMARY_PWY-3061 menthol biosynthesis
PathBank:SMP0014204 Monoterpenoid Biosynthesis
View All Pathways