Human Metabolome Database Version 3.5

Showing metabocard for Trioxilin A3 (HMDB01977)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:30 -0600
Update Date 2013-05-29 13:33:06 -0600
HMDB ID HMDB01977
Secondary Accession Numbers None
Metabolite Identification
Common Name Trioxilin A3
Description Trioxilin 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 Link_out).
Structure Thumb
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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 Formula C20H34O5
Average Molecular Weight 354.481
Monoisotopic Molecular Weight 354.240624198
IUPAC Name (5Z,9E,11R,12S,14Z)-8,11,12-trihydroxyicosa-5,9,14-trienoic acid
Traditional IUPAC Name trioxilin A3
CAS Registry Number 68860-46-8
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 Key WPLPEZUSILBTGP-CIQDQOFUSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Hydroxyeicosatrienoic 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 Parent Hydroxyeicosatrienoic Acids
Ontology
Status Expected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.047 g/L ALOGPS
LogP 4.53 ALOGPS
LogP 3.41 ChemAxon
LogS -3.88 ALOGPS
pKa (strongest acidic) 4.68 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 97.99 A2 ChemAxon
Rotatable Bond Count 15 ChemAxon
Refractivity 103.23 ChemAxon
Polarizability 40.59 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022775
KNApSAcK ID Not Available
Chemspider ID 4446329 Link_out
KEGG Compound ID C14809 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB01977 Link_out
Metagene Link HMDB01977 Link_out
METLIN ID Not Available
PubChem Compound 5283208 Link_out
PDB ID Not Available
ChEBI ID 36203 Link_out
References
Synthesis Reference Not 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 Link_out