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Record Information
Version4.0
Creation Date2006-05-22 14:17:30 UTC
Update Date2017-09-27 08:24:10 UTC
HMDB IDHMDB0001977
Secondary Accession Numbers
  • HMDB01977
Metabolite Identification
Common NameTrioxilin A3
DescriptionTrioxilin A3 is the enzymatically formed derivative of Hepoxilin A3. Normal human epidermis incubated with exogenous AA produces 12-oxo-eicosatetraenoic acid (12-oxo-ETE), hepoxilin A3 (HxA3), and hepoxilin B3 (HxB3) through the 12- Lipoxygenase (LO) pathway. 12-LO is the major arachidonic acid (AA) oxygenation pathway in epidermal cells with total product formation generally exceeding cyclooxygenase activity. Platelet-type 12-LO has been found to be the predominant isoenzyme expressed in human and murine skin epidermis. Increased levels of nonesterified hepoxilins and trioxilins occur in the psoriatic scales. Normal human epidermis synthesized only one of the two possible 10-hydroxy epimers of HxB3 whose formation is probably catalyzed by 12-LO. Hepoxilins exert action on plasma permeability on skin, and induce a specific-receptor-dependent Ca2+ mobilization from endogenous sources and the release of AA and diacylglycerols. (PMID: 11851887 ).
Structure
Thumb
Synonyms
ValueSource
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoic acidChEBI
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acidChEBI
(8,11R,12S)-OH 5c9t14t-20:3ChEBI
(8,11R,12S)-OH 5c9t14t-C20:3ChEBI
8,11,12-TetaChEBI
8,11R,12S-TriOH 5c9t14c-20:3ChEBI
8,11R,12S-TriOH 5c9t14c-C20:3ChEBI
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoateGenerator
(5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoateGenerator
(5Z,9E,11R,12S,14Z)-8,11,12-Trihydroxyicosa-5,9,14-trienoateHMDB
(5Z,9E,11R,12S,14Z)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acidHMDB
8,11,12-Trihydroxy-5,9,14-eicosatrienoateHMDB
8,11,12-Trihydroxy-5,9,14-eicosatrienoic acidHMDB
8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoateHMDB
8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoic acidHMDB
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoic acid
Traditional Nametrioxilin A3
CAS Registry Number68860-46-8
SMILES
CCCCC\C=C/C[C@H](O)[C@H](O)\C=C\C(O)C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H34O5/c1-2-3-4-5-6-10-13-18(22)19(23)16-15-17(21)12-9-7-8-11-14-20(24)25/h6-7,9-10,15-19,21-23H,2-5,8,11-14H2,1H3,(H,24,25)/b9-7-,10-6-,16-15+/t17?,18-,19+/m0/s1
InChI KeyWPLPEZUSILBTGP-CIQDQOFUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentHydroxyeicosatrienoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP4.53ALOGPS
logP3.41ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)4.68ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity103.23 m³·mol⁻¹ChemAxon
Polarizability40.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0109000000-32057b85f8b26ed1923eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02ti-1913000000-317db6ad761ac5229259View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9810000000-a6f6761b8cb7bd092125View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-be9e9136d023c2d0c23dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-0936000000-bc633eb61e3eadac39b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8920000000-a441615b390fda432670View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022775
KNApSAcK IDNot Available
Chemspider ID4446329
KEGG Compound IDC14809
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283208
PDB IDNot Available
ChEBI ID36203
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Anton R, Camacho M, Puig L, Vila L: Hepoxilin B3 and its enzymatically formed derivative trioxilin B3 are incorporated into phospholipids in psoriatic lesions. J Invest Dermatol. 2002 Jan;118(1):139-46. [PubMed:11851887 ]