Azelaic acid (BioCAD00000007008)

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Metabolite Card

Formula: C9H16O4 (188.1049)
SMILES: OC(=O)CCCCCCCC(O)=O

Synonyms [en]

azelaic acid; nonanedioic acid; Finacea; Lepargylic acid; acidum azelaicum; Nonandisaeure

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Azelaic acid. 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: BioCAD00000007008). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Azelaic acid (AZA) is a naturally occurring saturated nine-carbon dicarboxylic acid (COOH (CH2)7-COOH). It possesses a variety of biological actions both in vitro and in vivo. Interest in the biological activity of AZA arose originally out of studies of skin surface lipids and the pathogenesis of hypochromia in pityriasis versicolor infection. Later, it was shown that Pityrosporum can oxidize unsaturated fatty acids to C8-C12 dicarboxylic acids that are cornpetitive inhibitors of tyrosinase in vitro. Azelaic acid was chosen for further investigation and development of a new topical drug for treating hyperpigmentary disorders for the following reasons: it possesses a middle-range of antityrosinase activity, is inexpensive, and more soluble to be incorporated into a base cream than other dicarboxylic acids. Azelaic acid is another option for the topical treatment of mild to moderate inflammatory acne vulgaris. It offers effectiveness similar to that of other agents without the systemic side effects of oral antibiotics or the allergic sensitization of topical benzoyl peroxide and with less irritation than tretinoin. Azelaic acid is less expensive than certain other prescription acne preparations, but it is much more expensive than nonprescription benzoyl peroxide preparations. Whether it is safe and effective when used in combination with other agents is not known. (PMID: 7737781, 8961845).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 123-99-9
  • CAS Registry Number: 26776-28-3
  • PubChem: 2266
  • ChEBI: ChEBI:48131
  • HMDB: HMDB0000784
  • HMDB: HMDB00784
  • LipidMaps: LMFA01170054
  • KEGG: C08261
  • BioCyc: CPD0-1265
  • NCBI MeSH: azelaic acid
  • Wikipedia: Azelaic_acid
  • DrugBank: DB00548
  • RefMet: RM0153048
  • MoNA: BAF_UVA_POS000876
  • MoNA: BAF_UVA_POS001383
  • MoNA: BAF_UVA_POS001384
  • MoNA: BAF_UVA_POS001385
  • MoNA: BAF_UVA_POS001386
  • MoNA: Bruker_HCD_library000962
  • MoNA: CCMSLIB00000578346
  • MoNA: CCMSLIB00005463621
  • MoNA: CCMSLIB00005463622
  • MoNA: CCMSLIB00005463658
  • MoNA: EMBL-MCF_spec81944
  • MoNA: EMBL_MCF_2_0_HRMS_Library000266
  • MoNA: FiehnLib001112
  • MoNA: HMDB0000784_c_ms_1478
  • MoNA: HMDB0000784_ms_ms_1119
  • MoNA: HMDB0000784_ms_ms_1120
  • MoNA: HMDB0000784_ms_ms_1121
  • MoNA: KO000123
  • MoNA: KO000124
  • MoNA: KO000125
  • MoNA: KO000126
  • MoNA: KO000127
  • MoNA: MoNA016605
  • MoNA: MoNA016872
  • MoNA: MoNA023833
  • MoNA: MoNA032452
  • MoNA: MoNA032453
  • MoNA: MoNA032454
  • MoNA: MoNA037304
  • MoNA: PR311034
  • MoNA: VF-NPL-LTQ000315
  • MoNA: VF-NPL-LTQ000316
  • MoNA: VF-NPL-LTQ000318
  • MoNA: VF-NPL-LTQ006865
  • MoNA: VF-NPL-LTQ006866
  • MoNA: VF-NPL-LTQ006867
  • MoNA: VF-NPL-LTQ006868
  • MoNA: VF-NPL-QEHF000604
  • MoNA: VF-NPL-QEHF000605
  • MoNA: VF-NPL-QEHF000606
  • MoNA: VF-NPL-QEHF000607
  • MoNA: VF-NPL-QEHF000608
  • MoNA: VF-NPL-QEHF000609
  • MoNA: VF-NPL-QEHF011743
  • MoNA: VF-NPL-QEHF011744
  • MoNA: VF-NPL-QEHF011745
  • MoNA: VF-NPL-QEHF011746
  • MoNA: VF-NPL-QEHF011747
  • MoNA: VF-NPL-QEHF011748
  • MoNA: VF-NPL-QEHF011749
  • MoNA: VF-NPL-QEHF011750
  • MoNA: VF-NPL-QEHF011751
  • MoNA: VF-NPL-QEHF011752
  • MoNA: VF-NPL-QEHF011753
  • MoNA: VF-NPL-QEHF011754
  • MoNA: VF-NPL-QEHF011755
  • MoNA: VF-NPL-QEHF011756
  • MoNA: VF-NPL-QEHF011757
  • MoNA: VF-NPL-QTOF006818
  • MoNA: VF-NPL-QTOF006819
  • MoNA: VF-NPL-QTOF006820
  • Metlin: METLIN_5750
  • Coconut NaturalProduct: CNP0225848.0

Class / Ontology

Metabolic Network
ID EC Number Name
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Organism Source

Taxonomy Source

  1. Achillea biebersteinii [ncbi taxid: 282722]
  2. Acrisione denticulata [ncbi taxid: 462376]
  3. Agave cocui [ncbi taxid: 2695066]
  4. Alcyonium coralloides [ncbi taxid: 124279]
  5. Aloe africana [ncbi taxid: 1080010]
  6. Aloe ferox [ncbi taxid: 117798]
  7. Aloe spicata [ncbi taxid: 992642]
  8. Aloe vera [ncbi taxid: 34199]
  9. Amycolatopsis azurea [ncbi taxid: 36819]
  10. Angelica sinensis [ncbi taxid: 165353]
  11. Aplysina cauliformis [ncbi taxid: 289398]
  12. Archidendron ellipticum [ncbi taxid: 392766]
  13. Artemisia scoparia [ncbi taxid: 72351]
  14. Asplenium normale [ncbi taxid: 78467]
  15. Baccharis dracunculifolia [ncbi taxid: 72900]
  16. Berberis orthobotrys [ncbi taxid: 1433323]
  17. Blumea eriantha [ncbi taxid: ]
  18. Brucea javanica [ncbi taxid: 210348]
  19. Bulbinella floribunda [ncbi taxid: ]
  20. Calycotome villosa [ncbi taxid: ]
  21. Campanula hypopolia [ncbi taxid: 649658]
  22. Carpobrotus edulis [ncbi taxid: 379215]
  23. Carthamus oxyacantha [ncbi taxid: ]
  24. Caryocar villosum [ncbi taxid: 507520]
  25. Castanea crenata [ncbi taxid: 103480]
  26. Centrolobium tomentosum [ncbi taxid: 500182]
  27. Cephalonomia gallicola [ncbi taxid: 627714]
  28. Ceratophyllum submersum [ncbi taxid: 108412]
  29. Ceriops decandra [ncbi taxid: 172013]
  30. Chaenomeles sinensis [ncbi taxid: ]
  31. Chasmanthera dependens [ncbi taxid: 341015]
  32. Chelidonura fulvipunctata [ncbi taxid: ]
  33. Chiton tuberculatus [ncbi taxid: 1539881]
  34. Cichorium glandulosum [ncbi taxid: 1405821]
  35. Cichorium intybus [ncbi taxid: 13427]
  36. Cipadessa fruticosa [ncbi taxid: ]
  37. Citrullus lanatus [ncbi taxid: 3654]
  38. Cladonia impexa [ncbi taxid: ]
  39. Cladosporium cucumerinum [ncbi taxid: 166633]
  40. Cleome gynandra [ncbi taxid: ]
  41. Codium dwarkense [ncbi taxid: 1676211]
  42. Codonopsis pilosula [ncbi taxid: 86864]
  43. Colladonia triquetra [ncbi taxid: ]
  44. Corydalis pallida [ncbi taxid: 38903]
  45. Crepis czerepanovii [ncbi taxid: ]
  46. Cucurbita moschata [ncbi taxid: 3662]
  47. Cylindropuntia leptocaulis [ncbi taxid: 866983]
  48. Cymbastela coralliophila [ncbi taxid: 85786]
  49. Cynanchum atratum [ncbi taxid: ]
  50. Cynomorium songaricum [ncbi taxid: 627609]
  51. Dalbergia ecastaphyllum [ncbi taxid: 450024]
  52. Dendrobates auratus [ncbi taxid: 43471]
  53. Dioscorea japonica [ncbi taxid: 4673]
  54. Dioscorea opposita [ncbi taxid: ]
  55. Dioscorea polystachya [ncbi taxid: 55575]
  56. Diplazium esculentum [ncbi taxid: 29615]
  57. Dracocephalum kotschyi [ncbi taxid: 180015]
  58. Dytiscus marginalis [ncbi taxid: 398601]
  59. Eucalyptus camaldulensis [ncbi taxid: 34316]
  60. Eucalyptus globulus [ncbi taxid: 34317]
  61. Euonymus laxiflorus [ncbi taxid: 1009469]
  62. Eupatoriastrum nelsonii [ncbi taxid: ]
  63. Euphorbia formosana [ncbi taxid: 458693]
  64. Folium pini [ncbi taxid: ]
  65. Ganoderma lucidum [ncbi taxid: 5315]
  66. Glochidion philippicum [ncbi taxid: 271531]
  67. Herba artemisiae scopariae [ncbi taxid: ]
  68. Hibiscus syriacus [ncbi taxid: 106335]
  69. Himalaiella deltoidea [ncbi taxid: ]
  70. Homo sapiens [ncbi taxid: 9606]
  71. Huperzia selago [ncbi taxid: 70001]
  72. Hydroclathrus tenuis [ncbi taxid: 356642]
  73. Hymenoxys grandiflora [ncbi taxid: 2213171]
  74. Ilex brevicuspis [ncbi taxid: 53199]
  75. Kielmeyera rubriflora [ncbi taxid: ]
  76. Lactarius sanguifluus [ncbi taxid: 111137]
  77. Lagerstroemia speciosa [ncbi taxid: 122810]
  78. Larix lyallii [ncbi taxid: 71405]
  79. Lethariella sinensis [ncbi taxid: ]
  80. Lippia carviodora [ncbi taxid: ]
  81. Littorina littorea [ncbi taxid: 31216]
  82. Maackia floribunda [ncbi taxid: 53896]
  83. Meliosma wightii [ncbi taxid: ]
  84. Morus alba var. multicaulis [ncbi taxid: 170012]
  85. Myoporum platycarpum [ncbi taxid: 796003]
  86. Myrica nana [ncbi taxid: 385008]
  87. Ocimum gratissimum [ncbi taxid: 204144]
  88. Oecophylla smaragdina [ncbi taxid: 84561]
  89. Ongokea gore [ncbi taxid: 350425]
  90. Oplopanax elatus [ncbi taxid: 228659]
  91. Oroxylum indicum [ncbi taxid: 83951]
  92. Othonna tagetes [ncbi taxid: ]
  93. Palaquium canaliculatum [ncbi taxid: 3363855]
  94. Paracoccus denitrificans [ncbi taxid: 266]
  95. Parmelia metastrigosa [ncbi taxid: ]
  96. Pellina semitubulosa [ncbi taxid: ]
  97. Penicillium expansum [ncbi taxid: 27334]
  98. Phakellia flabellata [ncbi taxid: ]
  99. Philadelphus coronarius [ncbi taxid: 1403168]
  100. Phlojodicarpus sibiricus [ncbi taxid: 2893997]
  101. Phragmatobia fuliginosa [ncbi taxid: 214311]
  102. Phyllosticta cirsii [ncbi taxid: 1986016]
  103. Physalis sordida [ncbi taxid: 304128]
  104. Pithecellobium racemosum [ncbi taxid: ]
  105. Pneumatospora obcoronata [ncbi taxid: ]
  106. Polygala fruticosa [ncbi taxid: 375122]
  107. Psilostrophe cooperi [ncbi taxid: 128742]
  108. Pteris pedata [ncbi taxid: ]
  109. Pterocarpus macrocarpus [ncbi taxid: 108278]
  110. Ranunculus ternatus [ncbi taxid: 376254]
  111. Rhizoctonia repens [ncbi taxid: ]
  112. Russula lepida [ncbi taxid: 152963]
  113. Sanicula epipactis [ncbi taxid: 52473]
  114. Sarcophyton buitendijki [ncbi taxid: 358794]
  115. Scandix pecten-veneris [ncbi taxid: 40909]
  116. Schnabelia tetradonta [ncbi taxid: ]
  117. Scopolia atropoides [ncbi taxid: ]
  118. Semen alpiniae katsumadai [ncbi taxid: ]
  119. Senecio heliopsis [ncbi taxid: ]
  120. Senecio miser [ncbi taxid: ]
  121. Sideritis tragoriganum [ncbi taxid: 155267]
  122. Simaba cuneata [ncbi taxid: ]
  123. Solanum jamaicense [ncbi taxid: 115665]
  124. Solidago petiolaris [ncbi taxid: 72976]
  125. Sorbaria arborea [ncbi taxid: 32248]
  126. Streptomyces nigra 452T [ncbi taxid: ]
  127. Streptomyces purpurogeneiscleroticus [ncbi taxid: 68259]
  128. Streptomyces roseoverticillatus [ncbi taxid: 66429]
  129. Syzygium levinei [ncbi taxid: 1009507]
  130. Tabernaemontana divaricata [ncbi taxid: 52861]
  131. Taonia australasica [ncbi taxid: ]
  132. Taxus drupacea [ncbi taxid: ]
  133. Thalictrum podocarpum [ncbi taxid: 1084686]
  134. Trichilia catigua [ncbi taxid: 1640457]
  135. Trichoplusia ni [ncbi taxid: 7111]
  136. Trifolium alexandrinum [ncbi taxid: 97006]
  137. Tripteris microcarpa [ncbi taxid: 662753]
  138. Turbina corymbosa [ncbi taxid: ]
  139. Urginea riparia [ncbi taxid: ]
  140. Ventilago madraspatana [ncbi taxid: 345802]
  141. Vincetoxicum atratum [ncbi taxid: 157443]
  142. Yponomeuta malinellus [ncbi taxid: 33466]
  143. Zaluzania grayana [ncbi taxid: 191180]
  144. Zanthoxylum acutifolium [ncbi taxid: ]

Pathway Synthetic

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