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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-14 00:36:18 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004692
Secondary Accession Numbers
  • HMDB04692
Metabolite Identification
Common Name12(R)-HPETE
Description12(R)-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 act in sequence to convert arachidonic acid via 12(R)-HPETE to 12(R)-HETE and the corresponding epoxyalcohol, 8(R)-hydroxy-11(R),12(R)-epoxyeicosatrienoic acid. The epidermal lipoxygenases 12R-LOX and eLOX3 are the gene products of ALOX12B and ALOXE3. Mutations in ALOXE3 or ALOX12B have been found in families with autosomal-recessive congenital ichthyosis (ARCI). ARCI is a clinically and genetically heterogeneous group of severe hereditary keratinization disorders characterized by intense scaling of the whole integument, and differences in color and shape, often associated with erythema. Mutations in ALOXE3 and ALOX12B on chromosome 17p13, which code for two different epidermal lipoxygenases, were found in patients with ichthyosiform erythroderma. Genetic studies indicated that 12R-lipoxygenase (12R-LOX) or epidermal lipoxygenase-3 (eLOX3) was mutated in six families affected by non-bullous congenital ichthyosiform erythroderma (NCIE), one of the main clinical forms of ichthyosis. (PMID: 16116617 , 15629692 ).
Structure
Data?1582752312
Synonyms
ValueSource
(5Z,8Z,10E,14Z)-(12R)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoic acidChEBI
(5Z,8Z,10E,14Z)-(12R)-12-Hydroperoxyicosa-5,8,10,14-tetraenoic acidChEBI
(5Z,8Z,10E,14Z)-(12R)-12-Hydroperoxyeicosa-5,8,10,14-tetraenoateGenerator
(5Z,8Z,10E,14Z)-(12R)-12-Hydroperoxyicosa-5,8,10,14-tetraenoateGenerator
12R-HpETEHMDB
12R-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoateHMDB
12R-Hydroperoxy-5Z,8Z,10E,14Z-eicosatetraenoic acidHMDB
12R-HydroperoxyeicosatetraenoateHMDB
12R-Hydroperoxyeicosatetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z,10E,12R,14Z)-12-hydroperoxyicosa-5,8,10,14-tetraenoic acid
Traditional Name12R-HpETE
CAS Registry Number126873-49-2
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-/m1/s1
InChI KeyZIOZYRSDNLNNNJ-ZYBDYUKJSA-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
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 Solubility0.0017 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
Polarizability39.88 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]+193.89531661259
DarkChem[M-H]-191.07831661259
DeepCCS[M+H]+193.01130932474
DeepCCS[M-H]-190.65330932474
DeepCCS[M-2H]-223.53930932474
DeepCCS[M+Na]+199.10530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12(R)-HPETECCCCC\C=C/C[C@@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O4123.6Standard polar33892256
12(R)-HPETECCCCC\C=C/C[C@@H](OO)\C=C\C=C/C\C=C/CCCC(O)=O2442.4Standard non polar33892256
12(R)-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(R)-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(R)-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(R)-HPETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nml-8491000000-0127633b6ae0909f16722017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(R)-HPETE GC-MS (1 TMS) - 70eV, Positivesplash10-05dr-9334000000-7ccf269dc3d82ad47d272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12(R)-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(R)-HPETE 10V, Positive-QTOFsplash10-014i-0119000000-19caf32dc0daf75104b32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 20V, Positive-QTOFsplash10-00ou-5975000000-f4a0ca5c1a3a9fb036e32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 40V, Positive-QTOFsplash10-052f-9640000000-496b0d1583282ff834662017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 10V, Negative-QTOFsplash10-000i-0119000000-f328ff1db02305a6bcd02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 20V, Negative-QTOFsplash10-014r-1659000000-87c05812516016895a3b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 40V, Negative-QTOFsplash10-0a4i-9740000000-43688cc7fb27bb45f0c92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 10V, Negative-QTOFsplash10-000i-0009000000-7847d679fdeeabe385732021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 20V, Negative-QTOFsplash10-0udr-0329000000-d4296bbebfcef533338a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 40V, Negative-QTOFsplash10-056u-3690000000-c9e5a737326ebfdd3bf02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 10V, Positive-QTOFsplash10-0f79-0249000000-702a285b6044fb920d292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 20V, Positive-QTOFsplash10-0f79-7977000000-3cd8fc7d5c58fa9ef0002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12(R)-HPETE 40V, Positive-QTOFsplash10-066u-9420000000-b47740fabc6ca56ad6c02021-09-24Wishart 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 IDFDB023408
KNApSAcK IDNot Available
Chemspider ID7827808
KEGG Compound IDC14812
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9548885
PDB IDNot Available
ChEBI ID34145
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferencePorter, Ned A.; Dussault, Patrick; Breyer, Robert A.; Kaplan, Jere; Morelli, Joseph. The resolution of racemic hydroperoxides: a chromatography-based separation of perketals derived from arachidonic, linoleic, and oleic acid hydroperoxides. Chemical Research in Toxicology (1990), 3(3), 236-43.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Eckl KM, Krieg P, Kuster W, Traupe H, Andre F, Wittstruck N, Furstenberger G, Hennies HC: Mutation spectrum and functional analysis of epidermis-type lipoxygenases in patients with autosomal recessive congenital ichthyosis. Hum Mutat. 2005 Oct;26(4):351-61. [PubMed:16116617 ]
  2. Yu Z, Schneider C, Boeglin WE, Brash AR: Mutations associated with a congenital form of ichthyosis (NCIE) inactivate the epidermal lipoxygenases 12R-LOX and eLOX3. Biochim Biophys Acta. 2005 Jan 5;1686(3):238-47. [PubMed:15629692 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Converts arachidonic acid to 12R- hydroperoxyeicosatetraenoic acid (12R-HPETE)
Gene Name:
ALOX12B
Uniprot ID:
O75342
Molecular weight:
80354.9