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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-14 00:46:16 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004696
Secondary Accession Numbers
  • HMDB04696
Metabolite Identification
Common Name11(R)-HPETE
Description11R-HPETE is a hydroperoxyeicosatetraenoic acid eicosanoid derived from arachidonic acid. 11R-HPETE is formed from arachidonic acid in the prostaglandin endoperoxide H synthase-1 cyclooxygenase site. 11R-HPETE has been described in other mammalian tissues (rat, sheep). There are two distinct isozymes of prostaglandin H synthase (PGHS), the key enzyme in prostaglandin biosynthesis; PGHS-1 is generally considered to play a housekeeping role, whereas PGHS-2 has been linked to various pathological processes. Both PGHS isozymes have two catalytic activities; they are a cyclooxygenase activity that converts arachidonic acid (AA) to prostaglandin G2 (PGG2) and a peroxidase activity that catalyzes the transformation of PGG2 to prostaglandin H2. Oxygenase activity is completely abolished in aspirin-treated PGHS-1 (ASA-PGHS-1), whereas aspirin-treated PGHS-2 (ASA-PGHS-2) still catalyzes formation of 11(R)-HPETE. (PMID: 12664566 , 15292194 , 15964853 , 12167656 ).
Structure
Data?1582752312
Synonyms
ValueSource
(5Z,8Z,12E,14Z)-(11R)-Hydroperoxyeicosa-5,8,12,14-tetraenoic acidChEBI
(5Z,8Z,12E,14Z)-(11R)-Hydroperoxyicosa-5,8,12,14-tetraenoic acidChEBI
(5Z,8Z,12E,14Z)-(11R)-Hydroperoxyeicosa-5,8,12,14-tetraenoateGenerator
(5Z,8Z,12E,14Z)-(11R)-Hydroperoxyicosa-5,8,12,14-tetraenoateGenerator
11R-HpETEHMDB
11R-Hydroperoxy-5Z,8Z,12E,14Z-eicosatetraenoateHMDB
11R-Hydroperoxy-5Z,8Z,12E,14Z-eicosatetraenoic acidHMDB
11-HPETEHMDB
11-Hydroperoxyeicosa-5,8,12,14-tetraenoic acidHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z,11R,12E,14Z)-11-hydroperoxyicosa-5,8,12,14-tetraenoic acid
Traditional Name11R-HpETE
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C=C/[C@@H](C\C=C/C\C=C/CCCC(O)=O)OO
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-7-10-13-16-19(24-23)17-14-11-8-6-9-12-15-18-20(21)22/h6-7,9-11,13-14,16,19,23H,2-5,8,12,15,17-18H2,1H3,(H,21,22)/b9-6-,10-7-,14-11-,16-13+/t19-/m0/s1
InChI KeyPCGWZQXAGFGRTQ-WXMXURGXSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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
logP5.89ALOGPS
logP5.81ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
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
Polarizability39.81 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]+191.46831661259
DarkChem[M-H]-188.83731661259
DeepCCS[M+H]+192.72130932474
DeepCCS[M-H]-190.36330932474
DeepCCS[M-2H]-223.94830932474
DeepCCS[M+Na]+199.17530932474
AllCCS[M+H]+190.532859911
AllCCS[M+H-H2O]+187.732859911
AllCCS[M+NH4]+193.132859911
AllCCS[M+Na]+193.932859911
AllCCS[M-H]-187.932859911
AllCCS[M+Na-2H]-189.732859911
AllCCS[M+HCOO]-191.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
11(R)-HPETECCCCC\C=C/C=C/[C@@H](C\C=C/C\C=C/CCCC(O)=O)OO4150.6Standard polar33892256
11(R)-HPETECCCCC\C=C/C=C/[C@@H](C\C=C/C\C=C/CCCC(O)=O)OO2438.8Standard non polar33892256
11(R)-HPETECCCCC\C=C/C=C/[C@@H](C\C=C/C\C=C/CCCC(O)=O)OO2686.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
11(R)-HPETE,1TMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)OO2770.1Semi standard non polar33892256
11(R)-HPETE,1TBDMS,isomer #1CCCCC/C=C\C=C\[C@@H](C/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)OO3007.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 11(R)-HPETE GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-9471000000-271bb63dd76b6bd7b8dc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11(R)-HPETE GC-MS (1 TMS) - 70eV, Positivesplash10-00bi-9354000000-2959c2b13f6a1ffc1c172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 11(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 - 11(R)-HPETE 10V, Positive-QTOFsplash10-014i-0129000000-8b5a6ec5a8e93d4df43a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 20V, Positive-QTOFsplash10-066u-3984000000-590b1c3c5c54056cb03c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 40V, Positive-QTOFsplash10-05tf-9450000000-506a146ae5995f7e861a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 10V, Negative-QTOFsplash10-000i-0119000000-2fa6543aace6174694862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 20V, Negative-QTOFsplash10-01bi-1759000000-2745f772813cdf1b7cc22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 40V, Negative-QTOFsplash10-0abc-8940000000-2e7a4ba08bbea064bfa32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 10V, Negative-QTOFsplash10-000i-0009000000-037acca5a6f06fc04e812021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 20V, Negative-QTOFsplash10-0fri-0439000000-fc32ab242b97cc902d522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 40V, Negative-QTOFsplash10-03fr-2490000000-dd6ddbbb7a13b7a9f7ce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 10V, Positive-QTOFsplash10-0f79-0239000000-ff725d3da871fb6a8f102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 20V, Positive-QTOFsplash10-0gbi-7955000000-6e8f0bf04354feb6c23e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 11(R)-HPETE 40V, Positive-QTOFsplash10-014i-9310000000-8398f0c0ddd77514e7b52021-09-22Wishart 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 IDFDB023411
KNApSAcK IDNot Available
Chemspider ID7827809
KEGG Compound IDC14820
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9548886
PDB IDNot Available
ChEBI ID34127
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. Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. Epub 2005 Jun 17. [PubMed:15964853 ]
  2. Thuresson ED, Lakkides KM, Smith WL: PGG2, 11R-HPETE and 15R/S-HPETE are formed from different conformers of arachidonic acid in the prostaglandin endoperoxide H synthase-1 cyclooxygenase site. Adv Exp Med Biol. 2002;507:67-72. [PubMed:12664566 ]
  3. Harman CA, Rieke CJ, Garavito RM, Smith WL: Crystal structure of arachidonic acid bound to a mutant of prostaglandin endoperoxide H synthase-1 that forms predominantly 11-hydroperoxyeicosatetraenoic acid. J Biol Chem. 2004 Oct 8;279(41):42929-35. Epub 2004 Jul 30. [PubMed:15292194 ]
  4. Tsai AL, Palmer G, Wu G, Peng S, Okeley NM, van der Donk WA, Kulmacz RJ: Structural characterization of arachidonyl radicals formed by aspirin-treated prostaglandin H synthase-2. J Biol Chem. 2002 Oct 11;277(41):38311-21. Epub 2002 Aug 6. [PubMed:12167656 ]