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Record Information
Version1.0
Creation Date2016-10-03 18:13:23 UTC
Update Date2020-05-11 20:42:13 UTC
BMDB IDBMDB0011134
Secondary Accession Numbers
  • BMDB11134
Metabolite Identification
Common Name5-HETE
Description5-HETE, also known as 5S-HETE, 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. Thus, 5-HETE is considered to be an eicosanoid lipid molecule. 5-HETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
5-HydroxyeicosatetraenoateKegg
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoic acidKegg
5-Hydroxyeicosatetraenoic acidGenerator
(6E,8Z,11Z,14Z)-(5S)-5-Hydroxyicosa-6,8,11,14-tetraenoateGenerator
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidHMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoic acidHMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoic acidHMDB
5(S)-Hydroxyeicosatetraenoic acidHMDB
5S-HETEHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateHMDB
(S)-(e,Z,Z,Z)-5-Hydroxyeicosa-6,8,11,14-tetraenoateHMDB
5(S)-Hydroxy-6(e),8(Z),11(Z),14(Z)-eicosatetraenoateHMDB
5(S)-HydroxyeicosatetraenoateHMDB
5(S)-HETEHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoateHMDB
5(S)-Hydroxy-6-trans-8,11,14-cis-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5-L-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoateHMDB
5S-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,e,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-(+-)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, (e,Z,Z,Z)-isomerHMDB
5-Hydroxy-6,8,11,14-eicosatetraenoic acid, R-(e,Z,Z,Z)-isomerHMDB
(5S,6E,8Z,11Z,14Z)-5-Hydroxy-6,8,11,14-eicosatetraenoic acidHMDB
5S-Hydroxy-6,8,11,14-(e,Z,Z,Z)-eicosatetraenoic acidHMDB
FA(20:4(5-OH,6E,8Z,11Z,14Z))HMDB
FA(20:4(5S-OH,6E,8Z,11Z,14Z))HMDB
5-HETEHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5S,6E,8Z,11Z,14Z)-5-hydroxyicosa-6,8,11,14-tetraenoic acid
Traditional Name5-hydroxyeicosatetraenoic acid
CAS Registry Number70608-72-9
SMILES
CCCCC\C=C/C\C=C/C\C=C/C=C/[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(21)17-15-18-20(22)23/h6-7,9-10,12-14,16,19,21H,2-5,8,11,15,17-18H2,1H3,(H,22,23)/b7-6-,10-9-,13-12-,16-14+/t19-/m1/s1
InChI KeyKGIJOOYOSFUGPC-JGKLHWIESA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.88ALOGPS
logP5.36ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.47 m³·mol⁻¹ChemAxon
Polarizability38.13 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0011134
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001434
KNApSAcK IDC00000423
Chemspider ID4444314
KEGG Compound IDC04805
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link5-Hydroxyeicosatetraenoic_acid
METLIN ID6554
PubChem Compound5280733
PDB IDNot Available
ChEBI ID28209
References
Synthesis ReferenceNicolaou, K. C.; Ladduwahetty, T.; Taffer, I. M.; Zipkin, R. E. A general strategy for the synthesis of monohydroxyeicosatetraenoic acids. Total synthesis of 5(S)-hydroxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-HETE) and 12(S)-hydroxy-5,8,14(Z),10(E)-eicosatetraenoic acid (12-HETE). Synthesis (1986), (4), 344-7.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available