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Human Metabolome Database Version 3.5

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Showing metabocard for 12-HETE (HMDB06111)

Record Information
Version 3.5
Creation Date 2007-04-12 17:21:17 -0600
Update Date 2013-02-08 17:14:32 -0700
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
Download: MOL | SDF | SMILES | InChI
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 Comments
Blood Detected and Quantified
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0.00422 +/- 0.000292 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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0.35 +/- 0.25 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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6.42 +/- 0.74 uM Adult (>18 years old) Not Specified Normal HM Replicate Plasma (n=3)
Blood Detected and Quantified
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0.0526 +/- 0.0944 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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3.95 +/- 3.3 uM Adult (>18 years old) Not Specified Normal Pennington Plasma (n=70)
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.0 - 0.001 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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0.00091 +/- 0.00031 uM Adult (>18 years old) Both Normal Measured via MS/MS techniques from 4 pooled CSF...
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Cerebrospinal Fluid (CSF) Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Cerebral Vasospasm Symptomatic cerebral vasospasm Concentration...
Urine Detected and Quantified
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0.0000001 (0.00-0.0000001) umol/mmol creatinine Adult (>18 years old) Both Zellweger syndrome Not Available
Urine Detected and Quantified
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0.0000054 (0.0000035-0.0000074) umol/mmol creatinine Adult (>18 years old) Both Zellweger syndrome Not Available
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
      • http://www.metagene.de/program/d.prg?mp=ZELLWEGER%20SYNDROME
      Associated OMIM IDs
      • 214100 Link_out (Peroxisomal biogenesis defect)
      DrugBank 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 Not Available