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Record Information
Version3.6
Creation Date2006-05-22 14:17:30 UTC
Update Date2013-05-29 19:33:06 UTC
HMDB IDHMDB01977
Secondary Accession NumbersNone
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
  1. (5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoate
  2. (5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoic acid
  3. (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoate
  4. (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyeicosa-5,9,14-trienoic acid
  5. (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoate
  6. (5Z,9E,14Z)-(11R,12S)-8,11,12-Trihydroxyicosa-5,9,14-trienoic acid
  7. 8,11,12-Teta
  8. 8,11,12-Trihydroxy-5,9,14-eicosatrienoate
  9. 8,11,12-Trihydroxy-5,9,14-eicosatrienoic acid
  10. 8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoate
  11. 8,11R,12S-Trihydroxy-5Z,9E,14Z-eicosatrienoic acid
  12. Trioxilin A3
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 IUPAC 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
KingdomOrganic Compounds
Super ClassLipids
ClassEicosanoids
Sub ClassHydroxyeicosatrienoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Hydroxy Fatty Acids
  • Organic Compounds
  • Straight Chain Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • 1,2 Diol
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Secondary Alcohol
Direct ParentHydroxyeicosatrienoic Acids
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
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 Area97.99ChemAxon
Rotatable Bond Count15ChemAxon
Refractivity103.23ChemAxon
Polarizability40.59ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB01977
Metagene LinkHMDB01977
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