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Human Metabolome Database Version 2.5

 

Showing metabocard for 8-HETE (HMDB04679)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-14 01:14:06
Update Date 2010-06-02 17:20:51
Accession Number HMDB04679
Secondary Accession Numbers HMDB05080
Common Name 8-HETE
Description 8(S)-HETE is a naturally occurring hydroxyeicosatetraenoic acid eicosanoid. 8(S)-HETE is a strong activator of peroxisome proliferator-activated receptors (PPARs) alpha and a weak activator of PPAR gamma. PPARs are nuclear hormone receptors that regulate gene transcription in response to peroxisome proliferators and fatty acids. PPARs also play an important role in the regulation of adipocyte differentiation. It is unclear however what naturally occurring compounds activate each of the PPAR subtypes. Additionally, 8(S)-HETE is able to induce differentiation of preadipocytes. (PMID: 7592593, 9113987)
Synonyms
  1. 8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoic acid
  2. 8S-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoic acid
  3. (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid
  4. 8S-HETE
  5. 8(S)-Hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate
  6. 8S-hydroxy-5Z,9E,11Z,14Z-eicosatetraenoate
  7. (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoate
Chemical IUPAC Name (5Z,8S,9E,11Z,14Z)-8-hydroxyicosa-5,9,11,14-tetraenoic acid
Chemical Formula C20H32O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Hydroxyeicosapolyenoic acids
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 320.466
Monoisotopic Molecular Weight 320.235138
Isomeric SMILES CCCCCC=C/CC=C/C=C/[C@@H](O)CC=C/CCCC(O)=O
Canonical SMILES CCCCCC=CCC=CC=CC(O)CC=CCCCC(O)=O
KEGG Compound ID C14776 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB04679 Link Image
Metagene Link HMDB04679 Link Image
METLIN ID Not Available
PubChem Compound 5283154 Link Image
PubChem Substance 4266112 Link Image
ChEBI ID 34486 Link Image
CAS Registry Number 98462-03-4
InChI Identifier InChI=1/C20H32O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h6-7,9-11,13-14,16,19,21H,2-5,8,12,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,14-11-,16-13+/t19-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.65e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 5 [Predicted by PubChem via XLOGP]; 5.87 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Blood
  • Cerebrospinal Fluid
Tissue Location Not Available
Concentrations (Normal)
Biofluid Blood
Value 0.000512 +/- 0.000367 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Oxygenated lipids were quantified by Theresa L. Pedersen and John W. Newman at the USDA’s Western Human Nutrition Research Center, Davis, CA, and Lipomics Technologies, Inc.
References
  • Wishart DS, Knox C, Guo AC, Eisner R, Young N, Gautam B, Hau DD, Psychogios N, Dong E, Bouatra S, Mandal R, Sinelnikov I, Xia J, Jia L, Cruz JA, Lim E, Sobsey CA, Shrivastava S, Huang P, Liu P, Fang L, Peng J, Fradette R, Cheng D, Tzur D, Clements M, Lewis A, De Souza A, Zuniga A, Dawe M, Xiong Y, Clive D, Greiner R, Nazyrova A, Shaykhutdinov R, Li L, Vogel HJ, Forsythe I: HMDB: a knowledgebase for the human metabolome. Nucleic Acids Res. 2008 Oct 25. [PubMed Link Image]
  • Psychogios N, Hau DD, Peng J, Guo AC, Mandal R, Bouatra S, Sinelnikov I, Krishnamurthy R, Eisner R, Gautam B, Young N, Xia J, Knox C, Dong E, Huang P, Hollander Z, Pedersen TL, Smith SR, Bamforth F, Greiner R, McManus B, Newman JW, Goodfriend T, Wishart DS: The human serum metabolome. PLoS One. 2011 Feb 16;6(2):e16957. [PubMed Link Image]
Biofluid Blood
Value 0.000749 +/- 3.3E-5 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Not Available
References
  • Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. Epub 2010 Jul 29. [PubMed Link Image]
Biofluid CSF
Value 0.000055 +/- 0.000034 uM
Age Adult:>18 yrs old
Sex Both
Patient information Normal
Comments Measured via MS/MS techniques from 4 pooled CSF samples provided by TNO/NuGO – The Netherlands
References
  • John W. Newman, USDA ARS Western Human Nutrition Research Center, Davis CA (personal communication - March 2, 2009)
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Arachidonic Acid Metabolism SMP00075 Link Image map00590 Link Image
General References Not Available