12(R)-HPETE (BioCAD00000001892)

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Metabolite Card

Formula: C20H32O4 (336.23)
SMILES: CCCCC\C=C/C[C@@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O

Synonyms [en]

12(R)-HPETE; 12R-HpETE; 12R-hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acid; (5Z,8Z,10E,14Z)-(12R)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acid; (5Z,8Z,10E,14Z)-(12R)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoic acid; 12R-hydroperoxyeicosatetraenoate

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

12(R)-HPETE. 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: BioCAD00000001892). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

12(R)-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 act in sequence to convert arachidonic acid via 12(R)-HPETE to 12(R)-HETE and the corresponding epoxyalcohol, 8(R)-hydroxy-11(R),12(R)-epoxyeicosatrienoic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 are the gene products of ALOX12B and ALOXE3. Mutations in ALOXE3 or ALOX12B have been found in families with autosomal-recessive congenital ichthyosis (ARCI). ARCI is a clinically and genetically heterogeneous group of severe hereditary keratinization disorders characterized by intense scaling of the whole integument, and differences in color and shape, often associated with erythema. Mutations in ALOXE3 and ALOX12B on chromosome 17p13, which code for two different epidermal lipoxygenases, were found in patients with ichthyosiform erythroderma. Genetic studies indicated that 12R-lipoxygenase (12R-LOX) or epidermal lipoxygenase-3 (eLOX3) was mutated in six families affected by non-bullous congenital ichthyosiform erythroderma (NCIE), one of the main clinical forms of ichthyosis. (PMID: 16116617, 15629692).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 126873-49-2
  • PubChem: 9548885
  • ChEBI: ChEBI:34145
  • HMDB: HMDB0004692
  • LipidMaps: LMFA03060070
  • KEGG: C14812
  • RefMet: RM0149890
  • Metlin: METLIN_36322
  • Coconut NaturalProduct: CNP0083637.1
  • Coconut NaturalProduct: CNP0083637.5

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R07038 1.13.11.- arachidonate: oxygen 12-oxidoreductase
KEGG:R13044 4.2.1.152 12(R)-HPETE hydro-lyase
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Organism Source

Taxonomy Source

Pathway Synthetic

pathway id name
WikiPathways:WP4721 Eicosanoid metabolism via lipooxygenases (LOX)
WikiPathways:WP4586 Metabolism of alpha-linolenic acid
PathBank:SMP0120730 Leukotriene C4 Synthesis Deficiency
PathBank:SMP0000083 Acetylsalicylic Acid Action Pathway
PathBank:SMP0000087 Rofecoxib Action Pathway
PathBank:SMP0000094 Sulindac Action Pathway
PathBank:SMP0000104 Indomethacin Action Pathway
PathBank:SMP0000120 Naproxen Action Pathway
PathBank:SMP0000106 Meloxicam Action Pathway
PathBank:SMP0000693 Antrafenine Action Pathway
PathBank:SMP0000697 Flurbiprofen Action Pathway
PathBank:SMP0000701 Phenylbutazone Action Pathway
PathBank:SMP0000705 Tiaprofenic Acid Action Pathway
PathBank:SMP0000709 Salicylic Acid Action Pathway
PathBank:SMP0000075 Arachidonic Acid Metabolism
PathBank:SMP0000086 Ibuprofen Action Pathway
PathBank:SMP0000093 Diclofenac Action Pathway
PathBank:SMP0000098 Ketorolac Action Pathway
PathBank:SMP0000102 Bromfenac Action Pathway
PathBank:SMP0000114 Nabumetone Action Pathway
View All Pathways