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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-14 00:30:47 UTC
Update Date2022-03-07 02:49:21 UTC
HMDB IDHMDB0004688
Secondary Accession Numbers
  • HMDB04688
Metabolite Identification
Common NameHepoxilin A3
DescriptionHepoxilin A3 is an electrophilic eicosanoids synthesized during arachidonic acid oxidative metabolism, which can participate in the Michael addition reaction with glutathione (GSH, a major cellular antioxidant) catalyzed by the GSH-S-transferase (GST) family. GSH-adducts have been observed with molecules synthesized through the 12-lipoxygenase pathway. (PMID 12432937 ). Hepoxilins have biological actions that appear to have, as their basis, changes in intracellular concentrations of ions including calcium and potassium ions as well as changes in second messenger systems. Recent evidence suggests that the biological actions of the hepoxilins may be receptor-mediated as indicated from data showing the existence of hepoxilin-specific binding proteins in the human neutrophils. Such evidence also implicates the association of G-proteins both in hepoxilin-binding as well as in hepoxilin action. (PMID 7947989 ).
Structure
Data?1582752312
Synonyms
ValueSource
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoic acidChEBI
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyeicosa-5,9,14-trienoateGenerator
11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoateHMDB
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoic acidHMDB
Hexophilin a3HMDB
HXA3 CPDHMDB
8-EH-2HMDB
Hepoxilin aHMDB
(5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoateHMDB
(5Z,9E)-8-Hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,9-dienoic acidHMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoateHMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyeicosa-5,9,14-trienoic acidHMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoateHMDB
(5Z,9E,14Z)-(11S,12S)-11,12-Epoxy-8-hydroxyicosa-5,9,14-trienoic acidHMDB
8-Hydroxy-11,12-epoxyeicosa-5,9,14-trienoateHMDB
8-Hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoateHMDB
8-Hydroxy-11S,12S-epoxy-5Z,14Z,9E-eicosatrienoic acidHMDB
(5Z,9E,14Z)-(8XI,11R,12S)-11,12-epoxy-8-hydroxyicosa-5,9,14-trienoateHMDB
Hepoxilin a3MeSH
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5Z,9E)-8-hydroxy-10-[(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl]deca-5,9-dienoic acid
Traditional NameHXA3 cpd
CAS Registry Number85589-24-8
SMILES
CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-10-13-18-19(24-18)16-15-17(21)12-9-7-8-11-14-20(22)23/h6-7,9-10,15-19,21H,2-5,8,11-14H2,1H3,(H,22,23)/b9-7-,10-6-,16-15+/t17?,18-,19+/m0/s1
InChI KeySGTUOBURCVMACZ-CIQDQOFUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hepoxilins. These are eicosanoids containing an oxirane group attached to the fatty acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHepoxilins
Alternative Parents
Substituents
  • Hepoxilin
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Oxirane
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility0.0094 g/LALOGPS
logP5.57ALOGPS
logP4.57ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area70.06 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity99.72 m³·mol⁻¹ChemAxon
Polarizability38.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+189.53331661259
DarkChem[M-H]-187.01631661259
DeepCCS[M+H]+197.20830932474
DeepCCS[M-H]-194.56630932474
DeepCCS[M-2H]-229.14230932474
DeepCCS[M+Na]+204.36930932474
AllCCS[M+H]+192.032859911
AllCCS[M+H-H2O]+189.232859911
AllCCS[M+NH4]+194.632859911
AllCCS[M+Na]+195.332859911
AllCCS[M-H]-190.132859911
AllCCS[M+Na-2H]-191.832859911
AllCCS[M+HCOO]-193.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Hepoxilin A3CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O3932.1Standard polar33892256
Hepoxilin A3CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O2437.3Standard non polar33892256
Hepoxilin A3CCCCC\C=C/C[C@@H]1O[C@@H]1\C=C\C(O)C\C=C/CCCC(O)=O2635.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Hepoxilin A3,1TMS,isomer #1CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C2718.9Semi standard non polar33892256
Hepoxilin A3,1TMS,isomer #2CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C2635.3Semi standard non polar33892256
Hepoxilin A3,2TMS,isomer #1CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2688.4Semi standard non polar33892256
Hepoxilin A3,1TBDMS,isomer #1CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C2962.0Semi standard non polar33892256
Hepoxilin A3,1TBDMS,isomer #2CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(O)C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C2891.9Semi standard non polar33892256
Hepoxilin A3,2TBDMS,isomer #1CCCCC/C=C\C[C@@H]1O[C@@H]1/C=C/C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3167.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Hepoxilin A3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-02vi-8693000000-2485293cd435c17c3c1c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hepoxilin A3 GC-MS (2 TMS) - 70eV, Positivesplash10-00fs-9504200000-b478b5ac38b9ea2481202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hepoxilin A3 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Hepoxilin A3 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 - Hepoxilin A3 10V, Positive-QTOFsplash10-014i-0119000000-f183a896d40b122d34a62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Positive-QTOFsplash10-0100-3912000000-8c6e6837752424382cf92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Positive-QTOFsplash10-05tf-9320000000-fd16a39bb680bae04d1e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 10V, Negative-QTOFsplash10-000i-0029000000-babbe7e5cbfec6729e522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Negative-QTOFsplash10-014r-1849000000-46fca9cc7712fb3e78762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Negative-QTOFsplash10-0a4l-9510000000-19c94ffaa2521c24fe092017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 10V, Positive-QTOFsplash10-0gb9-0119000000-2cd5dffbb345957a17122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Positive-QTOFsplash10-0gb9-9447000000-9642f8a03a6be023dd7d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Positive-QTOFsplash10-014l-9100000000-81bd5dcd190a814469612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 10V, Negative-QTOFsplash10-000i-0009000000-9f5846a55564d3c61df32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 20V, Negative-QTOFsplash10-000i-1679000000-85590dd00f0e1fcb79da2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hepoxilin A3 40V, Negative-QTOFsplash10-00kf-8941000000-b2f817f4c6f5d27eefd82021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue Locations
  • Epidermis
  • Leukocyte
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000114 +/- 0.000087 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 IDFDB023406
KNApSAcK IDNot Available
Chemspider ID4573947
KEGG Compound IDC14808
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHepoxilin
METLIN ID7070
PubChem Compound5460414
PDB IDNot Available
ChEBI ID15631
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. Savidge TC, Newman PG, Pan WH, Weng MQ, Shi HN, McCormick BA, Quaroni A, Walker WA: Lipopolysaccharide-induced human enterocyte tolerance to cytokine-mediated interleukin-8 production may occur independently of TLR-4/MD-2 signaling. Pediatr Res. 2006 Jan;59(1):89-95. Epub 2005 Dec 2. [PubMed:16326999 ]
  2. Sutherland M, Schewe T, Nigam S: Biological actions of the free acid of hepoxilin A3 on human neutrophils. Biochem Pharmacol. 2000 Feb 15;59(4):435-40. [PubMed:10644052 ]
  3. Demin PM, Reynaud D, Pace-Asciak CR: Chemical synthesis and actions of 11,12-thiirano-hepoxilin A3. J Lipid Mediat Cell Signal. 1996 Jan;13(1):63-72. [PubMed:8998598 ]
  4. Murphy RC, Zarini S: Glutathione adducts of oxyeicosanoids. Prostaglandins Other Lipid Mediat. 2002 Aug;68-69:471-82. [PubMed:12432937 ]
  5. Mills L, Reynaud D, Pace-Asciak CR: Hepoxilin-evoked intracellular reorganization of calcium in human neutrophils: a confocal microscopy study. Exp Cell Res. 1997 Feb 1;230(2):337-41. [PubMed:9024792 ]
  6. Pace-Asciak CR, Reynaud D, Laneuville O, Grinstein S, Nigam S: Hepoxilin A3 inhibits agonist-evoked rise in free intracellular calcium in human neutrophils. Adv Exp Med Biol. 1997;400A:375-80. [PubMed:9547579 ]
  7. Mrsny RJ, Gewirtz AT, Siccardi D, Savidge T, Hurley BP, Madara JL, McCormick BA: Identification of hepoxilin A3 in inflammatory events: a required role in neutrophil migration across intestinal epithelia. Proc Natl Acad Sci U S A. 2004 May 11;101(19):7421-6. Epub 2004 May 3. [PubMed:15123795 ]
  8. Nigam S, Patabhiraman S, Ciccoli R, Ishdorj G, Schwarz K, Petrucev B, Kuhn H, Haeggstrom JZ: The rat leukocyte-type 12-lipoxygenase exhibits an intrinsic hepoxilin A3 synthase activity. J Biol Chem. 2004 Jul 9;279(28):29023-30. Epub 2004 May 3. [PubMed:15123652 ]
  9. Reynaud D, Demin PM, Sutherland M, Nigam S, Pace-Asciak CR: Hepoxilin signaling in intact human neutrophils: biphasic elevation of intracellular calcium by unesterified hepoxilin A3. FEBS Lett. 1999 Mar 12;446(2-3):236-8. [PubMed:10100848 ]
  10. Yu Z, Schneider C, Boeglin WE, Marnett LJ, Brash AR: The lipoxygenase gene ALOXE3 implicated in skin differentiation encodes a hydroperoxide isomerase. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9162-7. Epub 2003 Jul 24. [PubMed:12881489 ]
  11. Anton R, Puig L, Esgleyes T, de Moragas JM, Vila L: Occurrence of hepoxilins and trioxilins in psoriatic lesions. J Invest Dermatol. 1998 Apr;110(4):303-10. [PubMed:9540966 ]
  12. Pace-Asciak CR, Reynaud D, Rounova O, Demin P, Pivnitsky KK: Hepoxilin A3 is metabolized into its omega-hydroxy metabolite by human neutrophils. Adv Exp Med Biol. 1999;469:535-8. [PubMed:10667379 ]
  13. Dho S, Grinstein S, Corey EJ, Su WG, Pace-Asciak CR: Hepoxilin A3 induces changes in cytosolic calcium, intracellular pH and membrane potential in human neutrophils. Biochem J. 1990 Feb 15;266(1):63-8. [PubMed:2106877 ]
  14. Hurley BP, Siccardi D, Mrsny RJ, McCormick BA: Polymorphonuclear cell transmigration induced by Pseudomonas aeruginosa requires the eicosanoid hepoxilin A3. J Immunol. 2004 Nov 1;173(9):5712-20. [PubMed:15494523 ]
  15. Nigam S, Nodes S, Cichon G, Corey EJ, Pace-Asciak CR: Receptor-mediated action of hepoxilin A3 releases diacylglycerol and arachidonic acid from human neutrophils. Biochem Biophys Res Commun. 1990 Sep 28;171(3):944-8. [PubMed:2171511 ]
  16. Reynaud D, Rounova O, Demin PM, Pivnitsky KK, Pace-Asciak CR: Hepoxilin A3 is oxidized by human neutrophils into its omega-hydroxy metabolite by an activity independent of LTB4 omega-hydroxylase. Biochim Biophys Acta. 1997 Oct 18;1348(3):287-98. [PubMed:9366245 ]
  17. Pace-Asciak CR: Hepoxilins: a review on their cellular actions. Biochim Biophys Acta. 1994 Nov 17;1215(1-2):1-8. [PubMed:7947989 ]