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Record Information
Version1.0
Creation Date2016-09-30 23:08:50 UTC
Update Date2020-05-21 16:28:39 UTC
BMDB IDBMDB0004244
Secondary Accession Numbers
  • BMDB04244
Metabolite Identification
Common Name15(S)-HPETE
Description15(S)-HPETE, also known as 15S-hpete 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. Thus, 15(S)-hpete is considered to be an eicosanoid lipid molecule. 15(S)-HPETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
Synonyms
ValueSource
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoateChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acidChEBI
15-HydroperoxyeicosatetraenoateChEBI
15-Hydroperoxyeicosatetraenoic acidChEBI
15-HydroperoxyicosatetraenoateChEBI
15-Hydroperoxyicosatetraenoic acidChEBI
15S-HpETEChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acidHMDB
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoateHMDB
15S-HydroperoxyeicosatetraenoateHMDB
15S-Hydroperoxyeicosatetraenoic acidHMDB
14,15-Epoxyarachidonic acidHMDB
15-HPEAHMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomerHMDB
15-Hydroperoxyarachidonic acidHMDB
15-HPAAHMDB
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-5,8,11,14-eicosatetraenoic acidHMDB
Arachidonic acid 15-hydroperoxideHMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid
Traditional Name15(S)-hpete
CAS Registry Number70981-96-3
SMILES
CCCCC[C@H](OO)\C=C\C=C/C\C=C/C\C=C/CCCC(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)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1
InChI KeyBFWYTORDSFIVKP-VAEKSGALSA-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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Polarizability38.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-7691000000-10e52eac953fb64dc1a6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00vr-9343000000-559ae101ce63837aa2c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0129000000-35e1b05b3a271d79d7feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-3494000000-dfe60ca573a64c813441View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0abc-9650000000-4e66ed45e98b64d54b28View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-21ceecb44bdf804c0c4bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01bi-3189000000-29f754a5638ca1b0ae57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9150000000-81504e73ce15d31bbd08View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004244
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023349
KNApSAcK IDC00000400
Chemspider ID4444416
KEGG Compound IDC05966
BioCyc IDNot Available
BiGG ID47085
Wikipedia LinkNot Available
METLIN ID7039
PubChem Compound5280893
PDB IDNot Available
ChEBI ID15628
References
Synthesis ReferenceDussault, Patrick; Lee, In Quen. The total synthesis of 15(S)-HPETE (hydroperoxyeicosatetraenoic acid). Journal of Organic Chemistry (1992), 57(7), 1952-4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Protects the hemoglobin in erythrocytes from oxidative breakdown.
Gene Name:
GPX1
Uniprot ID:
P00435
Molecular weight:
22659.0
Reactions
15(S)-HPETE + 2 Glutathione → 15(S)-HETE + Oxidized glutathione + Waterdetails
General function:
Involved in arachidonate 12-lipoxygenase activity
Specific function:
Non-heme iron-containing dioxygenase that catalyzes the stereo-specific peroxidation of free and esterified polyunsaturated fatty acids generating a spectrum of bioactive lipid mediators. Converts arachidonic acid into 12-hydroperoxyeicosatetraenoic acid/12-HPETE and 15-hydroperoxyeicosatetraenoic acid/15-HPETE. Also converts linoleic acid to 13-hydroperoxyoctadecadienoic acid. May also act on (12S)-hydroperoxyeicosatetraenoic acid/(12S)-HPETE to produce hepoxilin A3. Probably plays an important role in the immune and inflammatory responses. Through the oxygenation of membrane-bound phosphatidylethanolamine in macrophages may favor clearance of apoptotic cells during inflammation by resident macrophages and prevent an autoimmune response associated with the clearance of apoptotic cells by inflammatory monocytes. In parallel, may regulate actin polymerization which is crucial for several biological processes, including macrophage function. May also regulate macrophage function through regulation of the peroxisome proliferator activated receptor signaling pathway. Finally, it is also involved in the cellular response to IL13/interleukin-13. In addition to its role in the immune and inflammatory responses, may play a role in epithelial wound healing in the cornea maybe through production of lipoxin A4. May also play a role in endoplasmic reticulum stress response and the regulation of bone mass.
Gene Name:
ALOX15
Uniprot ID:
P27479
Molecular weight:
75124.0
Reactions
Arachidonic acid + Oxygen → 15(S)-HPETEdetails