Human Metabolome Database Version 3.5

Showing metabocard for 12-HETE (HMDB06111)

Record Information
Version 3.5
Creation Date 2007-04-12 17:21:17 -0600
Update Date 2013-05-29 13:42:53 -0600
HMDB ID HMDB06111
Secondary Accession Numbers
  • HMDB04698
Metabolite Identification
Common Name 12-HETE
Description 12-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 Link_out, 12480795 Link_out, 17361113 Link_out, 8498970 Link_out,1333255 Link_out, 2119633 Link_out). 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
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Display: 2D Structure | 3D Structure
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 Formula C20H32O3
Average Molecular Weight 320.4663
Monoisotopic Molecular Weight 320.23514489
IUPAC Name (5E,8Z,10Z,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
Traditional IUPAC Name 12-hete
CAS Registry Number 71030-37-0
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 Key ZNHVWPKMFKADKW-FYMOKONMSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroxyeicosatetraenoic 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 Parent Hydroxyeicosatetraenoic Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0017 g/L ALOGPS
LogP 5.86 ALOGPS
LogP 5.36 ChemAxon
LogS -5.26 ALOGPS
pKa (strongest acidic) 4.89 ChemAxon
pKa (strongest basic) -1.6 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 14 ChemAxon
Refractivity 101.47 ChemAxon
Polarizability 38.84 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.00422 +/- 0.000292 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
0.35 +/- 0.25 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
6.42 +/- 0.74 uM Adult (>18 years old) Not Specified Comment Normal
Blood Detected and Quantified
0.0526 +/- 0.0944 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
3.95 +/- 3.3 uM Adult (>18 years old) Not Specified Comment Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.0 - 0.001 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
0.00091 +/- 0.00031 uM Adult (>18 years old) Both Comment Normal
  • John W. Newm...
Urine Detected and Quantified
0.000000078 (0.00-0.000000156) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected but not Quantified Not Applicable Adult (>18 years old) Both Comment Cerebral Vasospasm
Urine Detected and Quantified 0.0000082 (0.0000053-0.000011) umol/mmol creatinine Children (1-13 year old) Both Zellweger 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 Link_out
      Peroxisomal biogenesis defect
          Associated OMIM IDs
          • 214100 Link_out (Peroxisomal biogenesis defect)
          DrugBank ID Not Available
          DrugBank Metabolite ID Not Available
          Phenol Explorer Compound ID Not Available
          Phenol Explorer Metabolite ID Not Available
          FoodDB ID FDB001435
          KNApSAcK ID C00000424 Link_out
          Chemspider ID 4472408 Link_out
          KEGG Compound ID Not Available
          BioCyc ID Not Available
          BiGG ID Not Available
          Wikipedia Link Not Available
          NuGOwiki Link HMDB06111 Link_out
          Metagene Link HMDB06111 Link_out
          METLIN ID Not Available
          PubChem Compound 5312983 Link_out
          PDB ID Not Available
          ChEBI ID Not Available
          References
          Synthesis Reference Not 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 Link_out
          2. Simopoulos AP: Omega-3 fatty acids in inflammation and autoimmune diseases. J Am Coll Nutr. 2002 Dec;21(6):495-505. Pubmed: 12480795 Link_out
          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 Link_out
          4. Schror K: Prostaglandin-mediated actions of the renin-angiotensin system. Arzneimittelforschung. 1993 Feb;43(2A):236-41. Pubmed: 8498970 Link_out
          5. Ruzicka T: The role of the epidermal 12-hydroxyeicosatetraenoic acid receptor in the skin. Eicosanoids. 1992;5 Suppl:S63-5. Pubmed: 1333255 Link_out
          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 Link_out