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Showing metabocard for 15(S)-HETE (BMDB0003876)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:06:26 UTC
Update Date2020-05-21 16:28:39 UTC
BMDB IDBMDB0003876
Secondary Accession Numbers
  • BMDB03876
Metabolite Identification
Common Name15(S)-HETE
Description15-HETE, also known as 15S-hete or icomucret, 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, 15-HETE is considered to be an eicosanoid lipid molecule. 15-HETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoateChEBI
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoateChEBI
(15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acidChEBI
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoic acidChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoic acidChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoic acidChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoic acidChEBI
15(S)-Hydroxyeicosatetraenoic acidChEBI
15S-HETEChEBI
IcomucretChEBI
15(S)-HETEKegg
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acidGenerator
(15S)-15-Hydroxy-5,8,11-cis-13-trans-icosatetraenoic acidGenerator
(15S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateGenerator
(15S)-Hydroxyeicosa-(5Z,8Z,11Z,13E)-tetraenoateGenerator
(5Z,8Z,11Z,13E)-(15S)-15-Hydroxyicosa-5,8,11,13-tetraenoateGenerator
(5Z,8Z,11Z,13E,15S)-15-Hydroxy-5,8,11,13-eicosatetraenoateGenerator
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosa-5,8,11,13-tetraenoateGenerator
15(S)-HydroxyeicosatetraenoateGenerator
15-Hydroxy-5,8,11,13-eicosatetraenoic acidHMDB
15-Hydroxy-5,8,11,13-eicosatetraenoic acid, (S-(e,Z,Z,Z))-isomerHMDB
(15S)-15-Hydroxy-5,8,11-cis-13-trans-eicosic acidHMDB
(15S,5Z,8Z,11Z,13E)-15-HydroxyeicosatetraenoateHMDB
(15S,5Z,8Z,11Z,13E)-15-Hydroxyeicosatetraenoic acidHMDB
(S)-15-HETEHMDB
15 HeteHMDB
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoateHMDB
15(S)-Hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acidHMDB
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoateHMDB
15S-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acidHMDB
(5Z,8Z,11Z,13E,15S)-15-Hydroxyeicosatetraenoic acidHMDB
15(S)-Hydroxy-5,8,11-cis-13-trans-eicosatetraenoic acidHMDB
15(S)-Hydroxy-5Z,8Z,11Z,13E-eicosatetraenoic acidHMDB
15-Hydroxyeicosatetraenoic acidHMDB
15S-Hydroxy-5,8,11,13-(Z,Z,Z,e)-eicosatetraenoic acidHMDB
FA(20:4(5Z,8Z,11Z,13E,15-OH))HMDB
FA(20:4(5Z,8Z,11Z,13E,15S-OH))HMDB
15-HETEHMDB, MeSH
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,13E,15S)-15-hydroxyicosa-5,8,11,13-tetraenoic acid
Traditional Name15 hete
CAS Registry Number54845-95-3
SMILES
CCCCC[C@H](O)\C=C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-2-3-13-16-19(21)17-14-11-9-7-5-4-6-8-10-12-15-18-20(22)23/h4-5,8-11,14,17,19,21H,2-3,6-7,12-13,15-16,18H2,1H3,(H,22,23)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1
InChI KeyJSFATNQSLKRBCI-VAEKSGALSA-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
LogP4.405Not Available
Predicted Properties
PropertyValueSource
logP5.82ALOGPS
logP5.36ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
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
Polarizability38.15 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zml-8392000000-2392d150cc271ce3a20aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9224200000-28bb287a1a8aa8319f91View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-014i-0269000000-6b7e052cfd2bb97562deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0ldi-0398000000-ff190e7ef4788dc235b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pvi-0395000000-5aefff1d8848add1df10View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0pdi-0693000000-f4fd2c47e2e2d4e7686cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-004i-1591000000-9d6de8ee88a3df3306d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-004i-0920000000-2023bab46b9a229c4bcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-3900000000-133a226bf0eb8235ececView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-052g-3900000000-084e1bd7da1469eba9c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0aq9-5900000000-3d240e182d4edd31c981View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0059000000-c05583912116817f993dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0r99-5393000000-12d4bc503332183deaa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9740000000-536a9943ef814b845ee2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0019000000-c73882d7441506b152edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-2169000000-bf33f63d6dfd38c0babfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9130000000-9448e55ece175750c0fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0459000000-f09ca4984311e7651353View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-1973000000-22e0f4adf8c461582eabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-9710000000-f42bad5d652833e0ca31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0009000000-f96c871128e9efc2ab45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1249000000-87b24140b02466ab64c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9130000000-3363d939385a8427ba5eView in MoNA
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 IDHMDB0003876
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023242
KNApSAcK IDNot Available
Chemspider ID4444307
KEGG Compound IDC04742
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280724
PDB IDNot Available
ChEBI ID15558
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Glutathione peroxidase 1
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:
GPX1
Uniprot ID:
P00435
Molecular weight:
22659.0
Reactions
15(S)-HPETE + 2 Glutathione → 15(S)-HETE + Oxidized glutathione + Waterdetails