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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-04-12 23:21:17 UTC
Update Date2020-02-26 21:26:14 UTC
HMDB IDHMDB0006111
Secondary Accession Numbers
  • HMDB0004698
  • HMDB04698
  • HMDB06111
Metabolite Identification
Common Name12-HETE
Description12-Hydroxyeicosatetraenoic acid (CAS: 71030-37-0), also known as 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 the pathogenesis of hypertension and may mediate angiotensin II and TGFbeta induced mesangial cell abnormality in diabetic nephropathy. 12-HETE is markedly elevated in the psoriatic lesions. 12-HETE is a vasoconstrictor eicosanoid that contributes 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 hyperlipoproteinemia) 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 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. 12-HETE is found to be associated with peroxisomal biogenesis defect and Zellweger syndrome, which are inborn errors of metabolism.
Structure
Data?1582752374
Synonyms
ValueSource
(12S)-12-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acidChEBI
(5Z,8Z,10E,12S,14Z)-12-Hydroxyeicosa-5,8,10,14-tetraenoic acidChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyeicosa-5,8,10,14-tetraenoic acidChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyicosa-5,8,10,14-tetraenoic acidChEBI
12(S)-Hydroxy-5(Z),8(Z),10(e),14(Z)-eicosatetraenoic acidChEBI
12(S)-Hydroxy-5,8,14(Z),10(e)-eicosatetraenoic acidChEBI
12(S)-Hydroxyeicosatetraenoic acidChEBI
12S-HETEChEBI
(12S)-12-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoateGenerator
(5Z,8Z,10E,12S,14Z)-12-Hydroxyeicosa-5,8,10,14-tetraenoateGenerator
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyeicosa-5,8,10,14-tetraenoateGenerator
(5Z,8Z,10E,14Z)-(12S)-12-Hydroxyicosa-5,8,10,14-tetraenoateGenerator
12(S)-Hydroxy-5(Z),8(Z),10(e),14(Z)-eicosatetraenoateGenerator
12(S)-Hydroxy-5,8,14(Z),10(e)-eicosatetraenoateGenerator
12(S)-HydroxyeicosatetraenoateGenerator
(5Z,8Z,10E,14Z)-12-Hydroxy-5,8,10,14-eicosatetraenoic acidHMDB
12(S)-HETEHMDB
12(S)-Hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acidHMDB
12-Hydroxy-5,8,10,14-eicosatetraenoic acidHMDB
12-Hydroxy-5Z,8Z,10E,14Z-eicosatetraenoic acidHMDB
12-Hydroxyeicosatetraenoic acidHMDB
12-L-Hydroxy-5,8,10,14-eicosatetraenoic acidHMDB
12S-Hydroxy-5,8,10,14-(Z,Z,e,Z)-eicosatetraenoic acidHMDB
FA(20:4(5Z,8Z,10E,12-OH,14Z))HMDB
FA(20:4(5Z,8Z,10E,12S-OH,14Z))HMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
Traditional Name12S-hete
CAS Registry Number54397-83-0
SMILES
CCCCC\C=C/C[C@H](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+/t19-/m0/s1
InChI KeyZNHVWPKMFKADKW-LQWMCKPYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0lxy-8892000000-af669345c2f07af6464fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0149000000-30d66ea8fabdf9ad8be7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-1170-5894000000-a08e2339ff5012eb70cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9630000000-1125d69108467f1388e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-a230e97019aecf4548b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1249000000-3b11e114d7aa3c180372Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9820000000-08efc5f37c4b2f87360cSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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)Both
Normal
details
BloodDetected and Quantified0.0526 +/- 0.0944 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.00395 +/- 0.0033 uMAdult (>18 years old)Both
Normal
details
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
Normal
    • John W. Newman, U...
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Male
Normal
details
UrineDetected and Quantified0-0.00000001560 umol/mmol creatinineInfant (0-1 year old)BothNormal details
UrineDetected and Quantified0.000012138 +/- 0.0000035633 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified0-1.560e-08 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected but not Quantified Adult (>18 years old)Both
Cerebral Vasospasm
details
UrineDetected and Quantified0.000000078 (0.00-0.000000156) umol/mmol creatinineAdult (>18 years old)BothPeroxisomal biogenesis defect
    • MetaGene: Metabol...
details
UrineDetected and Quantified0.00001248 (0.0000090000-0.00001903) umol/mmol creatinineInfant (0-1 year 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. Mayatepek E, Lehmann WD: 12- and 15-hydroxyeicosatetraenoic acid are excreted in the urine of peroxisome-deficient patients: evidence for peroxisomal metabolism in vivo. Pediatr Res. 1996 Jan;39(1):146-9. [PubMed:8825400 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Associated OMIM IDs
  • 214100 (Peroxisomal biogenesis defect)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00000424
Chemspider IDNot Available
KEGG Compound IDC14777
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link12-Hydroxyeicosatetraenoic acid
METLIN IDNot Available
PubChem Compound5283155
PDB IDNot Available
ChEBI ID34146
Food Biomarker OntologyNot Available
VMH ID12HARACHD
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 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]