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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 21:48:43 UTC
Update Date2021-09-26 22:52:34 UTC
HMDB IDHMDB0244667
Secondary Accession NumbersNone
Metabolite Identification
Common Name15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid
Description15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid, also known as 14,15-epoxyarachidonic acid or 15-HPAA, 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. Based on a literature review very few articles have been published on 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 15-hydroperoxyicosa-5,8,11,13-tetraenoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
15-Hydroperoxyicosa-5,8,11,13-tetraenoateGenerator
14,15-Epoxyarachidonic acidHMDB
15-HPAAHMDB
15-HPEAHMDB
15-HPETEHMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acidHMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (e,Z,Z,Z)-isomerHMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomerHMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomerHMDB
15-Hydroperoxy-5,8,11,14-eicosatetraenoic acidHMDB
15-Hydroperoxyarachidonic acidHMDB
Arachidonic acid 15-hydroperoxideHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.472
Monoisotopic Molecular Weight336.23005951
IUPAC Name15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
Traditional Name15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
CAS Registry NumberNot Available
SMILES
CCCCCC(OO)C=CC=CCC=CCC=CCCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)
InChI KeyBFWYTORDSFIVKP-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
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
logP5.86ALOGPS
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
Polarizability39.65 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
DeepCCS[M+H]+181.14430932474
DeepCCS[M-H]-178.78630932474
DeepCCS[M-2H]-211.67130932474
DeepCCS[M+Na]+187.23730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
15-Hydroperoxyicosa-5,8,11,13-tetraenoic acidCCCCCC(OO)C=CC=CCC=CCC=CCCCC(O)=O4171.6Standard polar33892256
15-Hydroperoxyicosa-5,8,11,13-tetraenoic acidCCCCCC(OO)C=CC=CCC=CCC=CCCCC(O)=O2396.2Standard non polar33892256
15-Hydroperoxyicosa-5,8,11,13-tetraenoic acidCCCCCC(OO)C=CC=CCC=CCC=CCCCC(O)=O2642.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-7691000000-10e52eac953fb64dc1a62021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-03Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid 10V, Positive-QTOFsplash10-0udr-0259000000-5a2a85ed38ed47d64c702021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid 20V, Positive-QTOFsplash10-0f79-1896000000-b6c85b7e90a53a2752ab2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid 40V, Positive-QTOFsplash10-00l6-9810000000-898d59f193fb8d5136782021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid 10V, Negative-QTOFsplash10-0f79-0019000000-b91b825f9248bd953b5b2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid 20V, Negative-QTOFsplash10-0udi-0059000000-b88743639188b44f67832021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid 40V, Negative-QTOFsplash10-0002-8091000000-62e6f1d45410fc34c98c2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1396
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1440
PDB IDNot Available
ChEBI IDNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]