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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-29 12:42:11 UTC
Update Date2022-03-07 02:51:03 UTC
HMDB IDHMDB0011136
Secondary Accession Numbers
  • HMDB11136
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
Data?1582752872
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
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.9931661259
DarkChem[M-H]-187.80631661259
DeepCCS[M+H]+182.26130932474
DeepCCS[M-H]-179.90230932474
DeepCCS[M-2H]-212.78830932474
DeepCCS[M+Na]+188.35430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
19(S)-HETEC[C@H](O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O4100.1Standard polar33892256
19(S)-HETEC[C@H](O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O2297.8Standard non polar33892256
19(S)-HETEC[C@H](O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O2541.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
19(S)-HETE,1TMS,isomer #1C[C@@H](CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2738.4Semi standard non polar33892256
19(S)-HETE,1TMS,isomer #2C[C@H](O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2588.2Semi standard non polar33892256
19(S)-HETE,2TMS,isomer #1C[C@@H](CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2640.6Semi standard non polar33892256
19(S)-HETE,1TBDMS,isomer #1C[C@@H](CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2964.0Semi standard non polar33892256
19(S)-HETE,1TBDMS,isomer #2C[C@H](O)CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2833.3Semi standard non polar33892256
19(S)-HETE,2TBDMS,isomer #1C[C@@H](CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3137.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 19(S)-HETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-6292000000-1a4a0cc055f0f52bee8c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19(S)-HETE GC-MS (2 TMS) - 70eV, Positivesplash10-00vj-9635300000-ddd79a51cb3e293f5b4b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19(S)-HETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 19(S)-HETE GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 10V, Positive-QTOFsplash10-0udr-0069000000-bcd73cb5c2ca397146202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 20V, Positive-QTOFsplash10-0pbl-1293000000-7c8dfeee4766c9e44f522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 40V, Positive-QTOFsplash10-05mo-6890000000-4d27ffebd9931a2a54602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 10V, Negative-QTOFsplash10-014i-0029000000-23e9177a6684968df9392017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 20V, Negative-QTOFsplash10-0uxr-0059000000-7e85f8ef6206e7d6e99f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 40V, Negative-QTOFsplash10-0a4i-9061000000-39ff83e91f7f478109682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 10V, Negative-QTOFsplash10-014i-0009000000-e186d794a57d5ac55a7e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 20V, Negative-QTOFsplash10-0uxr-2029000000-db5df64eb5908fb6cf752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 40V, Negative-QTOFsplash10-0006-9220000000-683e467984277e91af8a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 10V, Positive-QTOFsplash10-0udi-1349000000-37252a205e1048fb66a72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 20V, Positive-QTOFsplash10-0f79-2931000000-bdbc26c045eb5d9cb2722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 19(S)-HETE 40V, Positive-QTOFsplash10-00l6-9800000000-312a8e774b71e9f31e1d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 24 proteins in total.

Enzymes

General function:
Involved in monooxygenase activity
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
General function:
Involved in monooxygenase activity
Specific function:
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:
CYP3A43
Uniprot ID:
Q9HB55
Molecular weight:
57756.285
General function:
Involved in monooxygenase activity
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. Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:
CYP1B1
Uniprot ID:
Q16678
Molecular weight:
60845.33
General function:
Involved in monooxygenase activity
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:
CYP2C18
Uniprot ID:
P33260
Molecular weight:
55710.075
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:
CYP2F1
Uniprot ID:
P24903
Molecular weight:
55500.64
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP4X1
Uniprot ID:
Q8N118
Molecular weight:
58874.62
General function:
Involved in monooxygenase activity
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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81

Only showing the first 10 proteins. There are 24 proteins in total.