Record Information
Version3.6
Creation Date2007-04-12 23:21:17 UTC
Update Date2013-05-29 19:42:53 UTC
HMDB IDHMDB06111
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.
Structure
Thumb
Synonyms
  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 IUPAC Name12-hete
CAS Registry Number71030-37-0
SMILES
CCCCC\C=C/CC(O)\C=C/C=C\C\C=C\CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7+,11-8-,13-10-,17-14-
InChI KeyZNHVWPKMFKADKW-FYMOKONMSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHydroxyeicosatetraenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
  • hydroxy monocarboxylic acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct ParentHydroxyeicosatetraenoic Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.0017 g/LALOGPS
logP5.86ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
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
refractivity101.47ChemAxon
polarizability38.84ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.00422 +/- 0.000292 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified0.35 +/- 0.25 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified6.42 +/- 0.74 uMAdult (>18 years old)Not SpecifiedCommentNormal
BloodDetected and Quantified0.0526 +/- 0.0944 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified3.95 +/- 3.3 uMAdult (>18 years old)Not SpecifiedCommentNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.0 - 0.001 uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified0.00091 +/- 0.00031 uMAdult (>18 years old)BothCommentNormal
  • John W. Newm...
UrineDetected and Quantified0.000000078 (0.00-0.000000156) umol/mmol creatinineAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentCerebral Vasospasm
UrineDetected and Quantified0.0000082 (0.0000053-0.000011) umol/mmol creatinineChildren (1-13 year old)BothZellweger syndrome
Associated Disorders and Diseases
Disease References
Cerebral vasospasm
  • 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
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
References
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