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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-13 15:05:29 UTC
Update Date2022-03-07 02:49:20 UTC
HMDB IDHMDB0004243
Secondary Accession Numbers
  • HMDB04243
Metabolite Identification
Common Name12(S)-HPETE
Description12-HPETE is one of the six monohydroperoxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid (Leukotrienes). Reduction of the hydroperoxide yields the more stable hydroxyl fatty acid (+/-)12-HETE. A family of biologically active compounds derived from arachidonic acid by oxidative metabolism through the 5-lipoxygenase pathway. They participate in host defense reactions and pathophysiological conditions such as immediate hypersensitivity and inflammation. They have potent actions on many essential organs and systems, including the cardiovascular, pulmonary, and central nervous system as well as the gastrointestinal tract and the immune system.
Structure
Data?1582752304
Synonyms
ValueSource
(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoateChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyicosa-5,8,10,14-tetraenoateChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acidChEBI
12-HpETEChEBI
12-HydroperoxyeicosatetraenoateChEBI
12-Hydroperoxyeicosatetraenoic acidChEBI
12-HydroperoxyicosatetraenoateChEBI
12-Hydroperoxyicosatetraenoic acidChEBI
12-OoheteChEBI
Arachidonic acid omega-9 hydroperoxideChEBI
Omega-9 hpaaChEBI
Omega-9-hydroperoxyarachidonic acidChEBI
(5Z,8Z,10E,14Z)-(12S)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoic acidGenerator
Arachidonate omega-9 hydroperoxideGenerator
Omega-9-hydroperoxyarachidonateGenerator
(5Z,8Z,10E,12S,14Z)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acidHMDB
(5Z,8Z,10E,12S,14Z)-12-Hydroperoxyicosa-5,8,10,14-tetraenoateHMDB
12-HPETE, (S-(e,e,e))-isomerHMDB
12-L-Hydroperoxy-5,8,10,14-eicosatetraenoic acidHMDB
12-Hydroperoxy-5,8,10,14-icosatetraenoic acidHMDB
12-HPETE, (e,Z,Z,Z)-isomerHMDB
12-HPETE, (S-(e,Z,Z,Z))-isomerHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z,10E,12S,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
Traditional Name12-HpETE
CAS Registry Number71774-10-2
SMILES
CCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-10-13-16-19(24-23)17-14-11-8-6-7-9-12-15-18-20(21)22/h7-11,13-14,17,19,23H,2-6,12,15-16,18H2,1H3,(H,21,22)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1
InChI KeyZIOZYRSDNLNNNJ-LQWMCKPYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroperoxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroperoxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroperoxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Allylic hydroperoxide
  • Hydroperoxide
  • Carboxylic acid derivative
  • Alkyl hydroperoxide
  • Carboxylic acid
  • Peroxol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Process

Naturally occurring process

Physical Properties
StateLiquid
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 Solubility0.0017 g/LALOGPS
logP5.9ALOGPS
logP5.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity102.82 m³·mol⁻¹ChemAxon
Polarizability39.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+193.08231661259
DarkChem[M-H]-190.79431661259
DeepCCS[M+H]+192.20630932474
DeepCCS[M-H]-189.84830932474
DeepCCS[M-2H]-222.73430932474
DeepCCS[M+Na]+198.29930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12(S)-HPETECCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O4123.6Standard polar33892256
12(S)-HPETECCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O2442.4Standard non polar33892256
12(S)-HPETECCCCC\C=C/C[C@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O2685.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12(S)-HPETE,1TMS,isomer #1CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)OO2764.4Semi standard non polar33892256
12(S)-HPETE,1TBDMS,isomer #1CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)OO3008.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 12(S)-HPETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nml-8491000000-0127633b6ae0909f16722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(S)-HPETE GC-MS (1 TMS) - 70eV, Positivesplash10-05dr-9334000000-7ccf269dc3d82ad47d272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(S)-HPETE 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 - 12(S)-HPETE 10V, Positive-QTOFsplash10-014i-0119000000-663dc7dd460df95c9d6d2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Positive-QTOFsplash10-00pl-5975000000-e3fe517c22245902e6d22015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Positive-QTOFsplash10-052f-9640000000-1c2eba4af6221c6ee4882015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 10V, Negative-QTOFsplash10-000i-0129000000-9b31acab4f79d4ab744c2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Negative-QTOFsplash10-014r-1659000000-5db483e2b6ae8fccb37e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Negative-QTOFsplash10-0a4i-9740000000-a88fa00904c08bd3dbfe2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 10V, Positive-QTOFsplash10-0f79-0249000000-702a285b6044fb920d292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Positive-QTOFsplash10-0f79-7977000000-3cd8fc7d5c58fa9ef0002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Positive-QTOFsplash10-066u-9420000000-b47740fabc6ca56ad6c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 10V, Negative-QTOFsplash10-000i-0009000000-7847d679fdeeabe385732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 20V, Negative-QTOFsplash10-0udr-0329000000-d4296bbebfcef533338a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(S)-HPETE 40V, Negative-QTOFsplash10-056u-3690000000-c9e5a737326ebfdd3bf02021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Locations
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.00145 +/- 0.0023 uMAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023348
KNApSAcK IDNot Available
Chemspider ID4444415
KEGG Compound IDC05965
BioCyc IDNot Available
BiGG ID44618
Wikipedia LinkNot Available
METLIN ID7038
PubChem Compound5280892
PDB IDNot Available
ChEBI ID15626
Food Biomarker OntologyNot Available
VMH ID12HPET
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNagata, Ryu; Kawakami, Masayuki; Matsuura, Teruo; Saito, Isao. Synthesis of 12-hydroperoxyeicosatetraenoic acid (12-HPETE). On the stereochemistry in the conversion of 12(S)-HETE to 12-HPETE. Tetrahedron Letters (1989), 30(21), 2817-20.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Boutaud O, Aronoff DM, Richardson JH, Marnett LJ, Oates JA: Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H(2) synthases. Proc Natl Acad Sci U S A. 2002 May 14;99(10):7130-5. [PubMed:12011469 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Oxygenase and 14,15-leukotriene A4 synthase activity.
Gene Name:
ALOX12
Uniprot ID:
P18054
Molecular weight:
75693.38
Reactions
Arachidonic acid + Oxygen → 12(S)-HPETEdetails