Isoleucine (BioCAD00000012594)

feces urine plant natural products marine natural products

Metabolite Card

Chinese Name: 异亮氨酸
Formula: C6H13NO2 (131.0946)
SMILES: 

CCC(C)C(N)C(O)=O

Synonyms [en]

Isoleucine; 2-amino-3-methylpentanoic acid; (±)-erythro-Isoleucine; H-Ile-OH; L-(+)-Isoleucine; (S)-Isoleucine

Note

(±)-erythro-Isoleucine is a flavouring ingredient, dietary supplement, and a nutrient. Branched-chain amino acids (BCAA) are essential amino acids whose carbon structure is marked by a branch point. These three amino acids are critical to human life and are particularly involved in stress, energy and muscle metabolism. BCAA supplementation as therapy, both oral and intravenous, in human health and disease holds great promise. BCAA denotes valine, isoleucine, and leucine which are branched chain essential amino acids. Despite their structural similarities, the branched amino acids have different metabolic routes, with valine going solely to carbohydrates, leucine solely to fats, and isoleucine to both. The different metabolism accounts for different requirements for these essential amino acids in humans: 12 mg/kg, 14 mg/kg, and 16 mg/kg of valine, leucine, and isoleucine respectively. Furthermore, these amino acids have different deficiency symptoms. Valine deficiency is marked by neurological defects in the brain, while isoleucine deficiency is marked by muscle tremors. BCAA are decreased in patients with liver disease such as hepatitis, hepatic coma, cirrhosis, extrahepatic biliary atresia, or portacaval shunt. Aromatic amino acids (AAA)-tyrosine, tryptophan, and phenylalanine (as well as methionine) are increased in these conditions. Valine, in particular, has been established as a useful supplemental therapy to the ailing liver. All the BCAA probably compete with AAA for absorption into the brain. Supplemental BCAA with vitamin B6 and zinc help normalize the BCAA:AAA ratio. The BCAA are not without side effects. Leucine alone, for example, exacerbates pellagra and can cause psychosis in pellagra patients by increasing excretion of niacin in the urine. Leucine may lower brain serotonin and dopamine. The ratio of leucine to other BCAA is greatest in pork, where leucine is 7 to 8 g and the other BCAA together are only 3 to 4 g (http://www.dcnutrition.com).

Cytoplasm Extracellular
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 1160211-67-5
  • CAS Registry Number: 1509-34-8
  • CAS Registry Number: 2095501-92-9
  • CAS Registry Number: 25796-94-5
  • CAS Registry Number: 26287-61-6
  • CAS Registry Number: 3107-04-8
  • CAS Registry Number: 3275-37-4
  • CAS Registry Number: 443-79-8
  • CAS Registry Number: 73-32-5
  • PubChem: 57397079
  • PubChem: 6306
  • PubChem: 791
  • ChEBI: ChEBI:38264
  • HMDB: HMDB00172
  • HMDB: HMDB0033923
  • KEGG: C16434
  • NCBI MeSH: 2-amino-3-methylpentanoic acid
  • Wikipedia: Isoleucine
  • RefMet: RM0204278
  • MoNA: AU515307
  • MoNA: BAF_UVA_POS000076
  • MoNA: BAF_UVA_POS000077
  • MoNA: BAF_UVA_POS000078
  • MoNA: CCMSLIB00003740031
  • MoNA: CCMSLIB00005463980
  • MoNA: CCMSLIB00005464055
  • MoNA: CCMSLIB00005720610
  • MoNA: CCMSLIB00005720628
  • MoNA: CE000609
  • MoNA: CE000610
  • MoNA: CE000611
  • MoNA: CE000612
  • MoNA: CE000613
  • MoNA: CE000614
  • MoNA: CE000615
  • MoNA: CE000616
  • MoNA: CE000617
  • MoNA: CE000618
  • MoNA: CE000619
  • MoNA: CE000620
  • MoNA: EMBL-MCF_spec23096
  • MoNA: EMBL-MCF_spec352816
  • MoNA: EMBL-MCF_spec352821
  • MoNA: EMBL-MCF_spec370588
  • MoNA: EMBL-MCF_spec370601
  • MoNA: EMBL-MCF_spec370606
  • MoNA: EMBL-MCF_spec377602
  • MoNA: EMBL-MCF_spec377605
  • MoNA: EMBL_MCF_2_0_HRMS_Library000222
  • MoNA: EMBL_MCF_2_0_HRMS_Library000361
  • MoNA: FiehnHILIC000452
  • MoNA: FiehnHILIC001272
  • MoNA: FiehnHILIC002022
  • MoNA: FiehnHILIC002774
  • MoNA: FiehnLib000726
  • MoNA: FiehnLib001035
  • MoNA: HMDB0033923_ms_ms_271
  • MoNA: HMDB0033923_ms_ms_272
  • MoNA: HMDB0033923_ms_ms_273
  • MoNA: MoNA001943
  • MoNA: MoNA001944
  • MoNA: MoNA001946
  • MoNA: MoNA016744
  • MoNA: MoNA024313
  • MoNA: MoNA024361
  • MoNA: MoNA032097
  • MoNA: MoNA032101
  • MoNA: MoNA032103
  • MoNA: MoNA032704
  • MoNA: MoNA032706
  • MoNA: MoNA032707
  • MoNA: MoNA034058
  • MoNA: MoNA034912
  • MoNA: MoNA035861
  • MoNA: MoNA035862
  • MoNA: MoNA035863
  • MoNA: MoNA036034
  • MoNA: MoNA036035
  • MoNA: MoNA036039
  • MoNA: MoNA037047
  • MoNA: MoNA037164
  • MoNA: MoNA037745
  • MoNA: MoNA037883
  • MoNA: MoNA038557
  • MoNA: PM018187
  • Metlin: METLIN_71198
  • Coconut NaturalProduct: CNP0018040.0
  • Coconut NaturalProduct: CNP0035023.0
  • Coconut NaturalProduct: CNP0057604.0
  • Coconut NaturalProduct: CNP0084337.0
  • Coconut NaturalProduct: CNP0317782.0
  • Coconut NaturalProduct: CNP0337843.1
  • Coconut NaturalProduct: CNP0337843.3
  • Coconut NaturalProduct: CNP0501927.1
  • metaboanalyst: 6c648ae0f049e19356b26c470c4e0a52
  • metaboanalyst: a1071832d33e7999d45b7cc5a58bf98c
  • metaboanalyst: b21bedc6ad66a69a66f9150871cb20ad
  • HERB: HBIN030865
  • HERB: HBIN033218

Class / Ontology

Metabolic Network
ID EC Number Name
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Mass Spectrum
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Organism Source

Taxonomy Source

  1. Homo sapiens [ncbi taxid: 9606]
  2. Abelmoschus esculentus [ncbi taxid: 455045]
  3. Actinidia chinensis [ncbi taxid: 3625]
  4. Agaricus bisporus [ncbi taxid: 5341]
  5. Ageratum conyzoides [ncbi taxid: 68299]
  6. Allium ampeloprasum [ncbi taxid: 4681]
  7. Allium ascalonicum [ncbi taxid: 1476995]
  8. Allium cepa [ncbi taxid: 4679]
  9. Allium fistulosum [ncbi taxid: 35875]
  10. Allium sativum [ncbi taxid: 4682]
  11. Allium schoenoprasum [ncbi taxid: 74900]
  12. Amelanchier alnifolia [ncbi taxid: 32219]
  13. Anacardium occidentale [ncbi taxid: 171929]
  14. Ananas comosus [ncbi taxid: 4615]
  15. Anarhichas lupus [ncbi taxid: 8204]
  16. Anethum graveolens [ncbi taxid: 40922]
  17. Annona cherimola [ncbi taxid: 49314]
  18. Anoplopoma fimbria [ncbi taxid: 229290]
  19. Anthriscus cerefolium [ncbi taxid: 40888]
  20. Apium graveolens [ncbi taxid: 4045]
  21. Arabidopsis thaliana [ncbi taxid: 3702]
  22. Arachis hypogaea [ncbi taxid: 3818]
  23. Archosargus probatocephalus [ncbi taxid: 119682]
  24. Arctium lappa [ncbi taxid: 4217]
  25. Armoracia rusticana [ncbi taxid: 3704]
  26. Artocarpus altilis [ncbi taxid: 194251]
  27. Artocarpus heterophyllus [ncbi taxid: 3489]
  28. Asparagus officinalis [ncbi taxid: 4686]
  29. Avena sativa [ncbi taxid: 4498]
  30. Averrhoa carambola [ncbi taxid: 28974]
  31. Basella alba [ncbi taxid: 3589]
  32. Belone belone [ncbi taxid: 129037]
  33. Bertholletia excelsa [ncbi taxid: 3645]
  34. Beta vulgaris [ncbi taxid: 161934]
  35. Bos taurus [ncbi taxid: 9913]
  36. Brassica juncea [ncbi taxid: 3707]
  37. Brassica napus [ncbi taxid: 3708]
  38. Brassica oleracea [ncbi taxid: 3712]
  39. Brassica oleracea var. sabauda [ncbi taxid: 1216010]
  40. Brassica rapa [ncbi taxid: 3711]
  41. Brassica ruvo [ncbi taxid: ]
  42. Brosimum alicastrum [ncbi taxid: 194253]
  43. Brosme brosme [ncbi taxid: 81638]
  44. Cajanus cajan [ncbi taxid: 3821]
  45. Calvatia fenzlii [ncbi taxid: 626502]
  46. Calvatia gigantea [ncbi taxid: 68762]
  47. Calvatia lilacina [ncbi taxid: 2979578]
  48. Camellia sinensis [ncbi taxid: 4442]
  49. Canarium ovatum [ncbi taxid: 43691]
  50. Capra aegagrus [ncbi taxid: 9923]
  51. Capsicum annuum [ncbi taxid: 4072]
  52. Carica papaya [ncbi taxid: 3649]
  53. Carthamus tinctorius [ncbi taxid: 4222]
  54. Carum carvi [ncbi taxid: 48032]
  55. Carya illinoinensis [ncbi taxid: 32201]
  56. Castanea sativa [ncbi taxid: 21020]
  57. Ceratonia siliqua [ncbi taxid: 20340]
  58. Chanos chanos [ncbi taxid: 29144]
  59. Chenopodium album [ncbi taxid: 3559]
  60. Chenopodium quinoa [ncbi taxid: 63459]
  61. Chlamydomonas reinhardtii [ncbi taxid: 3055]
  62. Cicer arietinum [ncbi taxid: 3827]
  63. Cichorium endivia [ncbi taxid: 114280]
  64. Cichorium intybus [ncbi taxid: 13427]
  65. Cinnamomum aromaticum [ncbi taxid: 119260]
  66. Cistanche deserticola [ncbi taxid: 161395]
  67. Citrullus lanatus [ncbi taxid: 3654]
  68. Citrus latifolia [ncbi taxid: ]
  69. Citrus limon [ncbi taxid: ]
  70. Citrus paradisi [ncbi taxid: ]
  71. Citrus reticulata [ncbi taxid: 85571]
  72. Citrus sinensis [ncbi taxid: 2711]
  73. Cocos nucifera [ncbi taxid: 13894]
  74. Coffea arabica [ncbi taxid: 13443]
  75. Coffea canephora [ncbi taxid: 49390]
  76. Colocasia esculenta [ncbi taxid: 4460]
  77. Corchorus olitorius [ncbi taxid: 93759]
  78. Coregonus artedi [ncbi taxid: 36181]
  79. Cornu saigae tataricae [ncbi taxid: ]
  80. Coryphaena hippurus [ncbi taxid: 34814]
  81. Crassostrea virginica [ncbi taxid: 6565]
  82. Cucumis melo [ncbi taxid: 3656]
  83. Cucumis sativus [ncbi taxid: 3659]
  84. Cucurbita maxima [ncbi taxid: 3661]
  85. Cucurbita moschata [ncbi taxid: 3662]
  86. Cucurbita pepo [ncbi taxid: 3663]
  87. Cyprinus carpio [ncbi taxid: 7962]
  88. Daucus carota [ncbi taxid: 4039]
  89. Dimocarpus longan [ncbi taxid: 128017]
  90. Dioscorea pentaphylla [ncbi taxid: 167592]
  91. Diospyros kaki [ncbi taxid: 35925]
  92. Diospyros virginiana [ncbi taxid: 13493]
  93. Eragrostis tef [ncbi taxid: 110835]
  94. Eriobotrya japonica [ncbi taxid: 32224]
  95. Escherichia coli [ncbi taxid: 562]
  96. Escherichia coli K12 [ncbi taxid: ]
  97. Eumetopias jubatus [ncbi taxid: 34886]
  98. Fagopyrum esculentum [ncbi taxid: 3617]
  99. Feijoa sellowiana [ncbi taxid: 260130]
  100. Ficus carica [ncbi taxid: 3494]
  101. Ficus simplicissima [ncbi taxid: 1822162]
  102. Flammulina velutipes [ncbi taxid: 38945]
  103. Foeniculum vulgare [ncbi taxid: ]
  104. FOOD SAKE [ncbi taxid: ]
  105. Fragaria x ananassa [ncbi taxid: 3747]
  106. Ginkgo biloba [ncbi taxid: 3311]
  107. Glycine max [ncbi taxid: 3847]
  108. Grifola frondosa [ncbi taxid: 5627]
  109. Helianthus annuus [ncbi taxid: 4232]
  110. Helianthus tuberosus [ncbi taxid: 4233]
  111. Hippoglossus hippoglossus [ncbi taxid: 8267]
  112. Homo sapiens [ncbi taxid: 9606]
  113. Hordeum vulgare [ncbi taxid: 4513]
  114. Hybanthus floribundus subsp. floribundus [ncbi taxid: 351361]
  115. Ictalurus punctatus [ncbi taxid: 7998]
  116. Ipomoea aquatica [ncbi taxid: 89636]
  117. Ipomoea batatas [ncbi taxid: 4120]
  118. Juglans cinerea [ncbi taxid: 91214]
  119. Juglans regia [ncbi taxid: 51240]
  120. Katsuwonus pelamis [ncbi taxid: 8226]
  121. Lablab purpureus [ncbi taxid: 35936]
  122. Lactuca sativa [ncbi taxid: 4236]
  123. Lagenaria siceraria [ncbi taxid: 3668]
  124. Leiostomus xanthurus [ncbi taxid: 59837]
  125. Lens culinaris [ncbi taxid: 3864]
  126. Lentinus edodes [ncbi taxid: ]
  127. Lepidium sativum [ncbi taxid: 33125]
  128. Lilium hansonii [ncbi taxid: 82318]
  129. Linum usitatissimum [ncbi taxid: 4006]
  130. Lophius piscatorius [ncbi taxid: 8074]
  131. Lopholatilus chamaeleonticeps [ncbi taxid: 390349]
  132. Lota lota [ncbi taxid: 69944]
  133. Lupinus albus [ncbi taxid: 3870]
  134. Macadamia integrifolia [ncbi taxid: 60698]
  135. Malus pumila [ncbi taxid: 283210]
  136. Mangifera indica [ncbi taxid: 29780]
  137. Manihot esculenta [ncbi taxid: 3983]
  138. Manilkara zapota [ncbi taxid: 3741]
  139. Maranta arundinacea [ncbi taxid: 210060]
  140. Medicago sativa [ncbi taxid: 3879]
  141. Melanogrammus aeglefinus [ncbi taxid: 8056]
  142. Mentha spicata [ncbi taxid: 29719]
  143. Mentha x piperita [ncbi taxid: 34256]
  144. Microstomus kitt [ncbi taxid: 106175]
  145. Molva molva [ncbi taxid: 163112]
  146. Moringa oleifera [ncbi taxid: 3735]
  147. Mus musculus [ncbi taxid: 10090]
  148. Musa acuminata [ncbi taxid: 4641]
  149. Musa x paradisiaca [ncbi taxid: 89151]
  150. Nasturtium officinale [ncbi taxid: 65948]
  151. Nelumbo nucifera [ncbi taxid: 4432]
  152. Nephrops norvegicus [ncbi taxid: 6829]
  153. Ocimum basilicum [ncbi taxid: 39350]
  154. Oenothera biennis [ncbi taxid: 3942]
  155. Olea europaea [ncbi taxid: 4146]
  156. Oncorhynchus gorbuscha [ncbi taxid: 8017]
  157. Oncorhynchus keta [ncbi taxid: 8018]
  158. Oncorhynchus kisutch [ncbi taxid: 8019]
  159. Oncorhynchus mykiss [ncbi taxid: 8022]
  160. Oncorhynchus nerka [ncbi taxid: 8023]
  161. Oncorhynchus tshawytscha [ncbi taxid: 74940]
  162. Ophiodon elongatus [ncbi taxid: 225387]
  163. Opuntia cochenillifera [ncbi taxid: ]
  164. Origanum vulgare [ncbi taxid: 39352]
  165. Oryza sativa [ncbi taxid: 4530]
  166. Pachyrhizus erosus [ncbi taxid: 109171]
  167. Panicum miliaceum [ncbi taxid: 4540]
  168. Papaver somniferum [ncbi taxid: 3469]
  169. Pastinaca sativa [ncbi taxid: 4041]
  170. Pediomelum esculentum [ncbi taxid: 458363]
  171. Peprilus triacanthus [ncbi taxid: 183653]
  172. Persea americana [ncbi taxid: 3435]
  173. Petroselinum crispum [ncbi taxid: 4043]
  174. Phaseolus lunatus [ncbi taxid: 3884]
  175. Phaseolus vulgaris [ncbi taxid: 3885]
  176. Phoenix dactylifera [ncbi taxid: 42345]
  177. Phyllostachys edulis [ncbi taxid: 38705]
  178. Pinus edulis [ncbi taxid: 3340]
  179. Piper nigrum [ncbi taxid: 13216]
  180. Pistacia vera [ncbi taxid: 55513]
  181. Pisum sativum [ncbi taxid: ]
  182. Pleurotus ostreatus [ncbi taxid: 5322]
  183. Pomatomus saltatrix [ncbi taxid: ]
  184. Porphyra laciniata [ncbi taxid: ]
  185. Portulaca oleracea [ncbi taxid: 46147]
  186. Pouteria sapota [ncbi taxid: 233744]
  187. Prunus armeniaca [ncbi taxid: 36596]
  188. Prunus avium [ncbi taxid: 42229]
  189. Prunus domestica [ncbi taxid: 3758]
  190. Prunus dulcis [ncbi taxid: 3755]
  191. Prunus persica [ncbi taxid: 3760]
  192. Prunus tomentosa [ncbi taxid: 105667]
  193. Psidium cattleianum [ncbi taxid: ]
  194. Psidium guajava [ncbi taxid: 120290]
  195. Psophocarpus tetragonolobus [ncbi taxid: 3891]
  196. Pyrus communis [ncbi taxid: 23211]
  197. Pyrus pyrifolia [ncbi taxid: 3767]
  198. Raphanus sativus [ncbi taxid: 3726]
  199. Reinhardtius hippoglossoides [ncbi taxid: 111784]
  200. Rheum rhabarbarum [ncbi taxid: 3621]
  201. Ribes nigrum [ncbi taxid: 78511]
  202. Rosmarinus officinalis [ncbi taxid: ]
  203. Rubus idaeus [ncbi taxid: 32247]
  204. Rumex acetosa [ncbi taxid: 41241]
  205. Saccharomyces cerevisiae [ncbi taxid: 4932]
  206. Salmo salar [ncbi taxid: 8030]
  207. Salvia hispanica [ncbi taxid: 49212]
  208. Scophthalmus maximus [ncbi taxid: 52904]
  209. Secale cereale [ncbi taxid: 4550]
  210. Sechium edule [ncbi taxid: ]
  211. Semen astragali complanati [ncbi taxid: ]
  212. Semen juglandis [ncbi taxid: ]
  213. Semen sojae praeparata [ncbi taxid: ]
  214. Sesamum orientale [ncbi taxid: ]
  215. Sesbania bispinosa [ncbi taxid: 485725]
  216. Shorea uliginosa [ncbi taxid: ]
  217. Sinapis alba [ncbi taxid: 3728]
  218. Solanum lycopersicum [ncbi taxid: 4081]
  219. Solanum melongena [ncbi taxid: 4111]
  220. Solanum tuberosum [ncbi taxid: 4113]
  221. Sonchus microcarpus [ncbi taxid: 329331]
  222. Sorghum bicolor [ncbi taxid: 4558]
  223. Spinacia oleracea [ncbi taxid: 3562]
  224. Stenodus leucichthys [ncbi taxid: 59296]
  225. Stenotomus chrysops [ncbi taxid: 35579]
  226. Strychnos diplotricha [ncbi taxid: 1040879]
  227. Sus scrofa [ncbi taxid: 9823]
  228. Syzygium aromaticum [ncbi taxid: 219868]
  229. Theobroma cacao [ncbi taxid: 3641]
  230. Thunnus alalunga [ncbi taxid: 8235]
  231. Thunnus albacares [ncbi taxid: 8236]
  232. Thunnus thynnus [ncbi taxid: 8237]
  233. Thymus vulgaris [ncbi taxid: 49992]
  234. Trigonella foenum-graecum [ncbi taxid: 78534]
  235. Triticosecale rimpaui [ncbi taxid: ]
  236. Triticum aestivum [ncbi taxid: 4565]
  237. Triticum durum [ncbi taxid: ]
  238. Triticum spelta [ncbi taxid: 58933]
  239. Triticum turanicum [ncbi taxid: ]
  240. Tussilago farfara [ncbi taxid: 118778]
  241. Undaria pinnatifida [ncbi taxid: 74381]
  242. Vaccinium corymbosum [ncbi taxid: 69266]
  243. Vaccinium macrocarpon [ncbi taxid: 13750]
  244. Valerianella locusta [ncbi taxid: 59166]
  245. Vicia faba [ncbi taxid: 3906]
  246. Vigna aconitifolia [ncbi taxid: 3918]
  247. Vigna angularis [ncbi taxid: 3914]
  248. Vigna mungo [ncbi taxid: 3915]
  249. Vigna radiata [ncbi taxid: 157791]
  250. Vigna unguiculata [ncbi taxid: 3917]
  251. Vitis vinifera [ncbi taxid: 29760]
  252. Xiphias gladius [ncbi taxid: 8245]
  253. Zea mays [ncbi taxid: 4577]
  254. Zingiber officinale [ncbi taxid: 94328]
  255. Allium sativum [ncbi taxid: 4682]
  256. Homo sapiens [ncbi taxid: 9606]

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