Coumarin (BioCAD00000008927)

saliva plant natural products microbial natural products

Metabolite Card

Formula: C9H6O2 (146.0368)
SMILES: O=C1OC2=CC=CC=C2C=C1

Synonyms [en]

coumarin; cumarin; Rattex; Tonka bean camphor; cis-o-Coumarinic acid lactone; Benzo-alpha-pyrone

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Coumarin. 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: BioCAD00000008927). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Coumarin belongs to the class of chemicals known as chromenones. Specifically it is a chromenone having the keto group located at the 2-position. A chromenone is a benzene molecule with two adjacent hydrogen atoms replaced by a lactone-like chain forming a second six-membered heterocycle that shares two carbons with the benzene ring. Coumarin is also described as a benzopyrone and is considered as a lactone. Coumarin is a colorless crystalline solid with a bitter taste and sweet odor resembling the scent of vanilla or the scent of newly-mowed or recently cut hay. It is a chemical poison found in many plants where it may serve as a chemical defense against predators. Coumarin occurs naturally in many plants and foods such as the tonka bean, woodruff, bison grass, cassia (bastard cinnamon or Chinese cinnamon), cinnamon, melilot (sweet clover), green tea, peppermint, celery, bilberry, lavender, honey (derived both from sweet clover and lavender), and carrots, as well as in beer, tobacco, wine, and other foodstuffs. Coumarin concentrations in these plants, spices, and foods range from <1 mg/kg in celery, to 7000 mg/kg in cinnamon, and up to 87,000 mg/kg in cassia. An estimate of human exposure to coumarin from the diet has been calculated to be 0.02 mg/kg/day. Coumarin is used as an additive in perfumes and fragranced consumer products at concentrations ranging from <0.5% To 6.4% In fine fragrances to <0.01% In detergents. An estimate for systemic exposure of humans from the use of fragranced cosmetic products is 0.04 mg/kg BW/day, assuming complete dermal penetration. The use of coumarin as a food additive was banned by the FDA in 1954 based on reports of hepatotoxicity in rats. It has clinical value as the precursor for several anticoagulants, notably warfarin. Coumarins, as a class, are comprised of numerous naturally occurring benzo-alpha-pyrone compounds with important and diverse physiological activities. Due to its potential hepatotoxic effects in humans, the European Commission restricted coumarin from naturals as a direct food additive to 2 mg/kg food/day, with exceptions granting higher levels for alcoholic beverages, caramel, chewing gum, and certain 'traditional foods'. In addition to human exposure to coumarin from dietary sources and consumer products, coumarin is also used clinically as an antineoplastic and for the treatment of lymphedema and venous insufficiency. Exposure ranges from 11 mg/day for consumption of natural food ingredients to 7 g/day following clinical administration. Although adverse effects in humans following coumarin exposure are rare, and only associated with clinical doses, recent evidence indicates coumarin causes liver tumors in rats and mice and Clara cell toxicity and lung tumors in mice. The multiple effects as well as the ongoing human exposure to coumarin have resulted in a significant research effort focused on understanding the mechanism of coumarin induced toxicity/carcinogenicity and its human relevance. These investigations have revealed significant species differences in coumarin metabolism and toxicity such that the mechanism of coumarin induced effects in rodents, and the relevance of these findings for the safety assessment of coumarin exposure in humans are now better understood. In October 2004, the European Food Safety Authority (EFSA, 2004) reviewed coumarin to establish a tolerable daily intake (TDI) in foods. EFSA issued an opinion indicating that coumarin is not genotoxic, and that a threshold approach to safety assessment was most appropriate. EFSA recommended a TDI of 0 to 0.1 Mg/kg BW/day. Including dietary contributions, the total human exposure is estimated to be 0.06 Mg/kg/day. As a pharmaceutical, coumarin has been used in diverse applications with a wide variety of dosing regimens. Unlike coumadin and other coumarin derivatives, coumarin has no anti-coagulant activity. However, at low doses (typically 7 to 10 mg/day), coumarin has been used as a 'venotonic' to promote vein health and small venule blood flow. Additionally, coumarin has been used clinically in the treatment of high-protein lymphedema arising from various etiologies. (PMID: 16203076).

Cytoplasm Extracellular Membrane
Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 103802-83-1
  • CAS Registry Number: 91-64-5
  • PubChem: 323
  • PubChem: 8144
  • ChEBI: ChEBI:28794
  • HMDB: HMDB0001218
  • HMDB: HMDB01218
  • KEGG: C05851
  • KEGG: D07751
  • BioCyc: COUMARIN
  • BioCyc: Coumarins
  • NCBI MeSH: coumarin
  • Wikipedia: Coumarin
  • DrugBank: DB04665
  • RefMet: RM0037517
  • MoNA: BML01352
  • MoNA: BML01359
  • MoNA: BML01366
  • MoNA: BML80985
  • MoNA: BML80987
  • MoNA: Bruker_HCD_library001010
  • MoNA: CCMSLIB00000424787
  • MoNA: CCMSLIB00005463770
  • MoNA: CCMSLIB00005463861
  • MoNA: FiehnHILIC000281
  • MoNA: FiehnHILIC001854
  • MoNA: FIO00033
  • MoNA: FIO00034
  • MoNA: FIO00035
  • MoNA: FIO00036
  • MoNA: FIO00037
  • MoNA: HMDB0001218_c_ms_1148
  • MoNA: HMDB0001218_ms_ms_1469
  • MoNA: HMDB0001218_ms_ms_1470
  • MoNA: HMDB0001218_ms_ms_1471
  • MoNA: JP001132
  • MoNA: JP007406
  • MoNA: JP009576
  • MoNA: MoNA033196
  • MoNA: MoNA033198
  • MoNA: MoNA033201
  • MoNA: MoNA036748
  • MoNA: MoNA036749
  • MoNA: MoNA036750
  • MoNA: MoNA037548
  • MoNA: MoNA038805
  • MoNA: NA002586
  • MoNA: NA002587
  • MoNA: NA002588
  • MoNA: NA002589
  • MoNA: NA002590
  • MoNA: NA002974
  • MoNA: NA002975
  • MoNA: NA002976
  • MoNA: NA002977
  • MoNA: NA002978
  • MoNA: NA003349
  • MoNA: NA003350
  • MoNA: NA003351
  • MoNA: NA003352
  • MoNA: NA003353
  • MoNA: NA003719
  • MoNA: NA003720
  • MoNA: NA003721
  • MoNA: NA003722
  • MoNA: NA003723
  • MoNA: PB004701
  • MoNA: PB004702
  • MoNA: PB004703
  • MoNA: SM817901
  • MoNA: VF-NPL-LTQ006571
  • MoNA: VF-NPL-LTQ006572
  • MoNA: VF-NPL-LTQ006573
  • MoNA: VF-NPL-LTQ006574
  • Metlin: METLIN_3525
  • Coconut NaturalProduct: CNP0225025.0
  • Coconut NaturalProduct: CNP0361457.1

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R04999 C05838<=>C05851 + C00001
KEGG:R12838 C05851 + C00004 + C00080<=>C02274 + C00003
BioCyc:RXN-8250 1.3.-.- PROTON + COUMARIN + NADPH --> DIHYDROCOUMARIN + NADP
BioCyc:RXN-8037 PROTON + CPD-7418 --> COUMARIN + WATER
View More
Organism Source

Taxonomy Source

  1. Alangium platanifolium [ncbi taxid: 60116]
  2. Alectoria japonica [ncbi taxid: ]
  3. Althaea officinalis [ncbi taxid: 145745]
  4. Alyxia lucida [ncbi taxid: ]
  5. Amburana cearensis [ncbi taxid: 149628]
  6. Amelanchier vulgaris [ncbi taxid: ]
  7. Angelica dahurica [ncbi taxid: 48101]
  8. Angelica decursiva [ncbi taxid: 52491]
  9. Angiopteris evecta [ncbi taxid: 13825]
  10. Aniba duckei [ncbi taxid: ]
  11. Anisodus tanguticus [ncbi taxid: 243964]
  12. Anthoxanthum odoratum L. [ncbi taxid: ]
  13. Aplysina laevis [ncbi taxid: ]
  14. Artemisia annua [ncbi taxid: 35608]
  15. Artemisia annua L. [ncbi taxid: ]
  16. Artemisia anomala [ncbi taxid: 714449]
  17. Artemisia capillaris [ncbi taxid: 265783]
  18. Asparagus officinalis [ncbi taxid: 4686]
  19. Aspergillus phoenicis [ncbi taxid: 5063]
  20. Asperula odora [ncbi taxid: ]
  21. Aster ageratoides [ncbi taxid: 714451]
  22. Aster oharai [ncbi taxid: 1544654]
  23. Astragalus zahlbruckneri [ncbi taxid: ]
  24. Axinella cannabina [ncbi taxid: 798305]
  25. Balanus glandula [ncbi taxid: 110520]
  26. Bufotes viridis [ncbi taxid: 30338]
  27. Butea superba [ncbi taxid: 480422]
  28. Byrsonima microphylla [ncbi taxid: 1801587]
  29. Calea pilosa [ncbi taxid: ]
  30. Callerya cinerea [ncbi taxid: 185709]
  31. Carlina acanthifolia [ncbi taxid: 143181]
  32. Cassipourea guianensis [ncbi taxid: 106621]
  33. Castanopsis eyrei [ncbi taxid: 425820]
  34. Cinamomum cassia [ncbi taxid: ]
  35. Cineraria geifolia [ncbi taxid: 82362]
  36. Cinnamomum aromaticum [ncbi taxid: 119260]
  37. Cinnamomum burmannii Nees ex BI [ncbi taxid: ]
  38. Cinnamomum cassia [ncbi taxid: ]
  39. Cinnamomum loureirii [ncbi taxid: ]
  40. Citrullus lanatus [ncbi taxid: 3654]
  41. Cnidium monieri [ncbi taxid: ]
  42. Cnidium monnieri [ncbi taxid: 94007]
  43. Colchicum decaisnei [ncbi taxid: 1094069]
  44. Conocybe siliginea [ncbi taxid: 373326]
  45. Conyza bonariensis [ncbi taxid: 91242]
  46. Coriandrum sativum [ncbi taxid: 4047]
  47. Corydalis ochotensis [ncbi taxid: 38907]
  48. Coussarea paniculata [ncbi taxid: 2321275]
  49. Crocodylus niloticus [ncbi taxid: 8501]
  50. Crotalaria madurensis [ncbi taxid: 890033]
  51. Croton penduliflorus [ncbi taxid: 2708777]
  52. Dactylaria lutea [ncbi taxid: ]
  53. Dalea tuberculata [ncbi taxid: ]
  54. Daucus carota [ncbi taxid: 4039]
  55. Daucus carota subsp. sativus (Hoffm.) Schuebl. & G. Martens [ncbi taxid: ]
  56. Delphinium cashmerianum [ncbi taxid: 1127149]
  57. Dendrilla membranosa [ncbi taxid: ]
  58. Dendroctonus ponderosae [ncbi taxid: 77166]
  59. Dendronephthya gigantea [ncbi taxid: 151771]
  60. Dianthus chinensis [ncbi taxid: 118431]
  61. Dianthus superbus [ncbi taxid: 288950]
  62. Diaporthe amygdali [ncbi taxid: 1214568]
  63. Diaporthe helianthi [ncbi taxid: 158607]
  64. Dictamnus gymnostylis [ncbi taxid: ]
  65. Dipteryx odorata [ncbi taxid: 53873]
  66. Dipteryx punctata [ncbi taxid: 1079074]
  67. Dolichandrone crispa [ncbi taxid: 1378001]
  68. Elaeis guineensis [ncbi taxid: 51953]
  69. Ephydatia syriaca [ncbi taxid: 1191330]
  70. Eremocarpus setiger [ncbi taxid: ]
  71. Eremostachys moluccelloides [ncbi taxid: ]
  72. Eucalyptus decorticans [ncbi taxid: 1711254]
  73. Eunicea pinta [ncbi taxid: 2734872]
  74. Eupatorium cannabinum [ncbi taxid: 102770]
  75. Eupatorium odoratum [ncbi taxid: ]
  76. Euphorbia characias [ncbi taxid: 3991]
  77. Euphorbia lathyris [ncbi taxid: 212925]
  78. Euryops rupestris [ncbi taxid: ]
  79. Fagopyrum esculentum [ncbi taxid: 3617]
  80. Ficus simplicissima [ncbi taxid: 1822162]
  81. Galium odoratum (L.) Scop. [ncbi taxid: ]
  82. Gelatoporia subvermispora [ncbi taxid: 42742]
  83. Glycyrrhiza glabra [ncbi taxid: 49827]
  84. Glycyrrhiza inflata [ncbi taxid: 74614]
  85. Glycyrrhiza uralensis [ncbi taxid: 74613]
  86. Gremmeniella abietina [ncbi taxid: 127520]
  87. Guarea trichilioides [ncbi taxid: ]
  88. Haldina cordifolia [ncbi taxid: 43493]
  89. Halocarpus biformis [ncbi taxid: 120592]
  90. Hansenia forbesii [ncbi taxid: 165499]
  91. Hansenia weberbaueriana [ncbi taxid: 54724]
  92. Helichrysum davenportii [ncbi taxid: ]
  93. Heliotropium amplexicaule [ncbi taxid: 168337]
  94. Heuchera cylindrica [ncbi taxid: 370361]
  95. Hierochloe odorata (L.) P. Beauv. [ncbi taxid: ]
  96. Holarrhena febrifuga [ncbi taxid: ]
  97. Holboellia fargesi [ncbi taxid: ]
  98. Homo sapiens [ncbi taxid: 9606]
  99. Hydrocotyle leucocephala [ncbi taxid: 554381]
  100. Hydrocotyle sibthorpioides [ncbi taxid: 4049]
  101. Hymenocallis speciosa [ncbi taxid: 146442]
  102. Hypericum carinatum [ncbi taxid: ]
  103. Hypericum japonicum [ncbi taxid: 282542]
  104. Hypoxylon carneum [ncbi taxid: 326655]
  105. Iberis amara [ncbi taxid: 190884]
  106. Impatiens siculifer [ncbi taxid: 253054]
  107. Impatiens sicullfer [ncbi taxid: ]
  108. Iochroma australe [ncbi taxid: ]
  109. Isodon gesneroides [ncbi taxid: 662912]
  110. Kloeckera brevis [ncbi taxid: ]
  111. Laetia corymbulosa [ncbi taxid: ]
  112. Lastrea thelypteris [ncbi taxid: ]
  113. Laurencia snyderiae [ncbi taxid: ]
  114. Lecidella chodati [ncbi taxid: ]
  115. Liatris squarrosa [ncbi taxid: 983230]
  116. Ligularia pleurocaulis [ncbi taxid: 262734]
  117. Litsea konishii [ncbi taxid: ]
  118. Litsea verticillata [ncbi taxid: 1009487]
  119. Lomatia silaifolia [ncbi taxid: 54945]
  120. Lonchocarpus salvadorensis [ncbi taxid: 3128864]
  121. Lychnophora columnaris [ncbi taxid: ]
  122. Maianthemum bifolium (L.) F. W. Schmidt [ncbi taxid: ]
  123. Maytenus hookeri [ncbi taxid: 205464]
  124. Melanophryniscus moreirae [ncbi taxid: 1903088]
  125. Melilotus albus Medik. [ncbi taxid: ]
  126. Melilotus altissimus Thuill. [ncbi taxid: ]
  127. Melilotus officinalis [ncbi taxid: 47083]
  128. Melilotus officinalis Lam. [ncbi taxid: ]
  129. Melittis melissophyllum L. [ncbi taxid: ]
  130. Menyanthes trifoliata L. [ncbi taxid: ]
  131. Mussaenda parviflora [ncbi taxid: 2100675]
  132. Nama johnstonii [ncbi taxid: ]
  133. Nepeta multifida [ncbi taxid: ]
  134. Nierembergia hippomanica [ncbi taxid: 144308]
  135. Nigritella suaveolens [ncbi taxid: ]
  136. Nocardia brasiliensis [ncbi taxid: 37326]
  137. Ophelia bicornis [ncbi taxid: 205107]
  138. Ophioglossum petiolatum [ncbi taxid: 37426]
  139. Osmanthus heterophyllus [ncbi taxid: 126555]
  140. Ostericum grosseserratum [ncbi taxid: 182415]
  141. Oyedaea verbesinoides [ncbi taxid: 183062]
  142. Panax papyrifer [ncbi taxid: ]
  143. Penicillium olsonii [ncbi taxid: 99116]
  144. Periploca calophylla [ncbi taxid: 413293]
  145. Petrorhagia dubia [ncbi taxid: 308175]
  146. Peucedanum praeruptorum [ncbi taxid: ]
  147. Phaleria cumingii [ncbi taxid: ]
  148. Picea abies [ncbi taxid: 3329]
  149. Pilocarpus spicatus [ncbi taxid: 549430]
  150. Piper sanctum [ncbi taxid: 511552]
  151. Plectranthus purpuratus [ncbi taxid: ]
  152. Pluchea suaveolens [ncbi taxid: ]
  153. Polygonum mite [ncbi taxid: ]
  154. Populus tomentosa [ncbi taxid: 118781]
  155. Prumnopitys ferruginoides [ncbi taxid: ]
  156. Prunus lusitanica [ncbi taxid: 194545]
  157. Pseudaegle trifoliata [ncbi taxid: ]
  158. pterocaulon sp. [ncbi taxid: ]
  159. Pulveroboletus retipes [ncbi taxid: 34440]
  160. Pyrola calliantha [ncbi taxid: 642526]
  161. Rabdosia loxothyrsa [ncbi taxid: ]
  162. Ranunculus acris [ncbi taxid: 3447]
  163. Rhododendron formosanum [ncbi taxid: 141212]
  164. Rhodopila globiformis [ncbi taxid: 1071]
  165. Scabiosa comosa [ncbi taxid: 1161150]
  166. Senecio rupestris [ncbi taxid: 121553]
  167. Solanum aculeatum [ncbi taxid: ]
  168. Solanum berthaultii [ncbi taxid: 47970]
  169. Sophora davidii [ncbi taxid: 49839]
  170. Sophora tometosa [ncbi taxid: ]
  171. Sphoeroides vermicularis [ncbi taxid: ]
  172. Stereocaulon leprocauloides [ncbi taxid: ]
  173. Stevia connata [ncbi taxid: 558454]
  174. Stichopus chloronotus [ncbi taxid: 240144]
  175. Streptomyces incarnatus [ncbi taxid: 665007]
  176. Streptomyces lomondensis [ncbi taxid: 68229]
  177. Streptomyces PM9 [ncbi taxid: ]
  178. Streptomyces rugosporus [ncbi taxid: 295838]
  179. Tephrosia pumila [ncbi taxid: 1383562]
  180. Tephrosia vogelii [ncbi taxid: 1157238]
  181. Tetrapanax papyriferus [ncbi taxid: ]
  182. Thaminophyllum multiflorum [ncbi taxid: ]
  183. Thorecta marginalis [ncbi taxid: ]
  184. Torilis japonica [ncbi taxid: 49576]
  185. Torresea cearensis [ncbi taxid: ]
  186. Trichomanes reniforme [ncbi taxid: ]
  187. Vepris louisii [ncbi taxid: 2709025]
  188. Verbascum thapsus [ncbi taxid: 39388]
  189. Vicia benghalensis [ncbi taxid: 154497]
  190. Virola sebifera [ncbi taxid: 224866]
  191. Vitis silvestris [ncbi taxid: ]
  192. Walsura tubulata [ncbi taxid: 124957]
  193. Xerula melanotricha [ncbi taxid: 302556]

Pathway Synthetic

pathway id name
BioCyc:META_PWY-5176 coumarin biosynthesis (via 2-coumarate)
BioCyc:META_PWY66-201 nicotine degradation IV
BioCyc:ARA_PWY-5176 coumarin biosynthesis (via 2-coumarate)
BioCyc:META_PWY-5319 coumarin metabolism (to melilotic acid)
BioCyc:THAPS_PWY-5176 coumarin biosynthesis (via 2-coumarate)
Plant Reactome:R-OSA-2744345 Metabolism and regulation
Plant Reactome:R-OSA-2744344 Secondary metabolism
Plant Reactome:R-OSA-1119284 Coumarin biosynthesis (via 2-coumarate)
PlantCyc:SPENNELLII_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:SUGARBEET_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:ALYRATA_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:TPARVULA_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:BRACHYPODIUM_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:CACUMINATA_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:CANNUUM_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:CARNATION_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:CARROT_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:RUBBERTREE_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:CLEMENTINE_PWY-5176 coumarin biosynthesis (via 2-coumarate)
PlantCyc:CSATIVA_PK_PWY-5176 coumarin biosynthesis (via 2-coumarate)
View All Pathways