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Record Information
Creation Date2007-04-12 23:21:17 UTC
Update Date2014-08-05 20:45:00 UTC
Secondary Accession Numbers
  • HMDB04698
Metabolite Identification
Common Name12-HETE
Description12-hydroxyeicosatetraenoic acid (12-HETE) is an eicosanoid, a 5-lipoxygenase metabolite of arachidonic acid. 5-Lipoxygenase (LO)-derived leukotrienes are involved in inflammatory glomerular injury. LO product 12-HETE is associated with pathogenesis of hypertension, and may mediate angiotensin II and TGFbeta induced mesengial cell abnormality in diabetic nephropathy. 12-HETE is markedly elevated in the psoriatic lesions. 12-HETE is a vasoconstrictor eicosanoid that contribute to high blood pressure in (renovascular) hypertension and pregnancy-induced hypertension. A significant percentage of patients suffering from a selective increase in plasma LDL cholesterol (type IIa hyperlipoproteinaemia) exhibits increased platelet reactivity. This includes enhanced platelet responsiveness against a variety of platelet-stimulating agents ex vivo and enhanced arachidonic acid metabolism associated with increased generation of arachidonic acid metabolites such as 12-HETE, and secretion of platelet-storage products. (PMID: 7562532 , 12480795 , 17361113 , 8498970 ,1333255 , 2119633 ). 12-HETE is a highly selective ligand used to label mu-opioid receptors in both membranes and tissue sections. The 12-s-HETE analog has been reported to augment tumour cell metastatic potential through activation of protein kinase c. 12-HETE can be formed either in the 12-S or 12-R configuration. It has a diversity of biological actions and is generated by a number of tissues including the renal glomerulus and the vasculature. 12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. 12-HETE is a neuromodulator that is synthesized during ischemia. Its neuronal effects include attenuation of calcium influx and glutamate release as well as inhibition of AMPA receptor (AMPA-R) activation.
  1. (E,Z,Z,Z)-12-hydroxy-5,8,10,14-Eicosatetraenoate
  2. (E,Z,Z,Z)-12-hydroxy-5,8,10,14-Eicosatetraenoic acid
  3. 12-HETE
  4. 12-Hydroxy-5,8,10,14-eicosatetraenoate
  5. 12-Hydroxy-5,8,10,14-eicosatetraenoic acid
  6. 12-Hydroxy-5E,8Z,10Z,14Z-eicosatetraenoate
  7. 12-Hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acid
  8. 12-Hydroxyeicosatetraenoate
  9. 12-Hydroxyeicosatetraenoic acid
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5E,8Z,10Z,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
Traditional Name12-hete
CAS Registry Number71030-37-0
InChI Identifier
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
Sub ClassHydroxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
  • hydroxy monocarboxylic acid(ChEBI)
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct ParentHydroxyeicosatetraenoic Acids
StatusDetected and Quantified
  • Endogenous
  • Food
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0017 g/LALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53ChemAxon
Rotatable Bond Count14ChemAxon
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BloodDetected and Quantified0.00422 +/- 0.000292 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.35 +/- 0.25 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00642 +/- 0.00074 uMAdult (>18 years old)Not Specified
BloodDetected and Quantified0.0526 +/- 0.0944 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00395 +/- 0.0033 uMAdult (>18 years old)Not Specified
Cerebrospinal Fluid (CSF)Detected and Quantified0.0 - 0.001 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.00091 +/- 0.00031 uMAdult (>18 years old)Both
    • John W. Newman, U...
UrineDetected and Quantified0.000000078 (0.00-0.000000156) umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Cerebral Vasospasm
UrineDetected and Quantified0.0000082 (0.0000053-0.000011) umol/mmol creatinineChildren (1-13 years old)BothZellweger syndrome details
Associated Disorders and Diseases
Disease References
Cerebral vasospasm
  1. Poloyac SM, Reynolds RB, Yonas H, Kerr ME: Identification and quantification of the hydroxyeicosatetraenoic acids, 20-HETE and 12-HETE, in the cerebrospinal fluid after subarachnoid hemorrhage. J Neurosci Methods. 2005 Jun 15;144(2):257-63. Epub 2004 Dec 30. Pubmed: 15910986
Peroxisomal biogenesis defect
  1. MetaGene
Associated OMIM IDs
  • 214100 (Peroxisomal biogenesis defect)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001435
KNApSAcK IDC00000424
Chemspider ID4472408
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06111
Metagene LinkHMDB06111
METLIN IDNot Available
PubChem Compound5312983
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Diaz A, Ruiz F, Florez J, Hurle MA, Pazos A: Mu-opioid receptor regulation during opioid tolerance and supersensitivity in rat central nervous system. J Pharmacol Exp Ther. 1995 Sep;274(3):1545-51. Pubmed: 7562532
  2. Simopoulos AP: Omega-3 fatty acids in inflammation and autoimmune diseases. J Am Coll Nutr. 2002 Dec;21(6):495-505. Pubmed: 12480795
  3. Hao CM, Breyer MD: Physiologic and pathophysiologic roles of lipid mediators in the kidney. Kidney Int. 2007 Jun;71(11):1105-15. Epub 2007 Mar 14. Pubmed: 17361113
  4. Schror K: Prostaglandin-mediated actions of the renin-angiotensin system. Arzneimittelforschung. 1993 Feb;43(2A):236-41. Pubmed: 8498970
  5. Ruzicka T: The role of the epidermal 12-hydroxyeicosatetraenoic acid receptor in the skin. Eicosanoids. 1992;5 Suppl:S63-5. Pubmed: 1333255
  6. Schror K: Platelet reactivity and arachidonic acid metabolism in type II hyperlipoproteinaemia and its modification by cholesterol-lowering agents. Eicosanoids. 1990;3(2):67-73. Pubmed: 2119633