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Showing Compound 12-HETE (FDB001435)

Record Information
Version1.0
Creation date2010-04-08 22:04:58 UTC
Update date2019-11-26 02:56:28 UTC
Primary IDFDB001435
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. 12-HETE is found in corn.
CAS Number71030-37-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
12-Hydroxy-5,8,10,14-eicosatetraenoic acidChEBI
12-Hydroxy-5,8,10,14-icosatetraenoic acidChEBI
12-Hydroxy-5,8,10,14-eicosatetraenoateGenerator
12-Hydroxy-5,8,10,14-icosatetraenoateGenerator
(E,Z,Z,Z)-12-hydroxy-5,8,10,14-Eicosatetraenoatebiospider
(E,Z,Z,Z)-12-hydroxy-5,8,10,14-Eicosatetraenoic acidbiospider
12-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoatebiospider
12-hydroxy-5E,8Z,10Z,14Z-eicosatetraenoic acidbiospider
12-Hydroxyarachidonic acidbiospider
12-hydroxyeicosatetraenoatebiospider
12-hydroxyeicosatetraenoic acidbiospider
5,8,10,14-Eicosatetraenoic acid, 12-hydroxy-, (E,Z,Z,Z)-biospider
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
Polarizability40.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H32O3
IUPAC name12-hydroxyicosa-5,8,10,14-tetraenoic acid
InChI IdentifierInChI=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)
InChI KeyZNHVWPKMFKADKW-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CCC(O)C=CC=CCC=CCCCC(O)=O
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS12-HETE, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0lxy-8892000000-af669345c2f07af6464fSpectrum
Predicted GC-MS12-HETE, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HETE, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HETE, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HETE, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HETE, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HETE, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12-HETE, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0139000000-8a72d1001d3d07756c042021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-5932000000-f79082fedeb294426f6f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9410000000-8748c14268773fb5c2fd2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-9fc7e9714470f0f9624f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0319000000-860117193f031a1697f12021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9581000000-d70c346b7a187ee4a2662021-10-12View Spectrum
NMRNot Available
ChemSpider ID4472408
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5312983
Pubchem Substance IDNot Available
ChEBI ID19138
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06111
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00000424
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia ID12-HETE
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.