Showing metabocard for 19(S)-HETE (BMDB0011136)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:13:26 UTC
Update Date2020-05-21 16:28:40 UTC
BMDB IDBMDB0011136
Secondary Accession Numbers
  • BMDB11136
Metabolite Identification
Common Name19(S)-HETE
Description19(S)-HETE, also known as 19-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, 19(S)-hete is considered to be an eicosanoid lipid molecule. 19(S)-HETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(19S)-Hydroxyeicosatetraenoic acidKegg
(19S)-Hydroxyicosatetraenoic acidKegg
(19S)-Hydroxy arachidonic acidKegg
(19S)-HydroxyeicosatetraenoateGenerator
(19S)-HydroxyicosatetraenoateGenerator
(19S)-Hydroxy arachidonateGenerator
(19S,5Z,8Z,11Z,14Z)-19-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
(5Z,8Z,11Z,14Z)-(19S)-19-Hydroxyeicosa-5,8,11,14-tetraenoic acidHMDB
(5Z,8Z,11Z,14Z,19S)-19-Hydroxyeicosa-5,8,11,14-tetraenoic acidHMDB
(5Z,8Z,11Z,14Z,19S)-19-Hydroxyicosa-5,8,11,14-tetraenoic acidHMDB
19(S)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoic acidHMDB
19(S)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoic acidHMDB
(19S,5Z,8Z,11Z,14Z)-19-Hydroxy-5,8,11,14-eicosatetraenoateHMDB
(5Z,8Z,11Z,14Z)-(19S)-19-Hydroxyeicosa-5,8,11,14-tetraenoateHMDB
(5Z,8Z,11Z,14Z,19S)-19-Hydroxyeicosa-5,8,11,14-tetraenoateHMDB
(5Z,8Z,11Z,14Z,19S)-19-Hydroxyicosa-5,8,11,14-tetraenoateHMDB
19(S)-Hydroxy-all-cis-5,8,11,14-eicosatetraenoateHMDB
19(S)-Hydroxyeicosa-5(Z),8(Z),11(Z),14(Z)-tetraenoateHMDB
19(S)-Hydroxyeicosatetraenoic acidHMDB
19-HETEHMDB
19-Hydroxy-5,8,11,14-eicosatetraenoic acidHMDB
Chemical FormulaC20H32O3
Average Molecular Weight320.4663
Monoisotopic Molecular Weight320.23514489
IUPAC Name(5Z,8Z,11Z,14Z,19S)-19-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name19S-hete
CAS Registry Number79551-85-2
SMILES
C[C@H](O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O3/c1-19(21)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-20(22)23/h3-6,9-12,19,21H,2,7-8,13-18H2,1H3,(H,22,23)/b5-3-,6-4-,11-9-,12-10-/t19-/m0/s1
InChI KeyXFUXZHQUWPFWPR-DZBJBCEBSA-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
logP5.8ALOGPS
logP5.12ChemAxon
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
Refractivity101.7 m³·mol⁻¹ChemAxon
Polarizability37.93 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, Positivesplash10-0005-6292000000-1a4a0cc055f0f52bee8cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00vj-9635300000-ddd79a51cb3e293f5b4bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0069000000-bcd73cb5c2ca39714620View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pbl-1293000000-7c8dfeee4766c9e44f52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-6890000000-4d27ffebd9931a2a5460View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0029000000-23e9177a6684968df939View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-0059000000-7e85f8ef6206e7d6e99fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9061000000-39ff83e91f7f47810968View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-e186d794a57d5ac55a7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-2029000000-db5df64eb5908fb6cf75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9220000000-683e467984277e91af8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1349000000-37252a205e1048fb66a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-2931000000-bdbc26c045eb5d9cb272View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00l6-9800000000-312a8e774b71e9f31e1dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011136
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027914
KNApSAcK IDNot Available
Chemspider ID7827806
KEGG Compound IDC14749
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9548883
PDB IDNot Available
ChEBI ID34185
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 2D14
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP2D14
Uniprot ID:
Q01361
Molecular weight:
56083.0
Reactions
Arachidonic acid + Oxygen → 19(S)-HETE + Waterdetails
Enzyme Details
2. Cytochrome P450 2U1
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase involved in the metabolism of arachidonic acid and its conjugates. Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase). Acts as an omega and omega-1 hydroxylase for arachidonic acid and possibly for other long chain fatty acids. May modulate the arachidonic acid signaling pathway and play a role in other fatty acid signaling processes. May downregulate the biological activities of N-arachidonoyl-serotonin, an endocannabinoid that has anti-nociceptive effects through inhibition of fatty acid amide hydrolase FAAH, TRPV1 receptor and T-type calcium channels. Catalyzes C-2 oxidation of the indole ring of N-arachidonoyl-serotonin forming a less active product 2-oxo-N-arachidonoyl-serotonin.
Gene Name:
CYP2U1
Uniprot ID:
Q0IIF9
Molecular weight:
61997.0
Reactions
Arachidonic acid + Oxygen → 19(S)-HETE + Waterdetails