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Bovine Metabolome Database



Showing metabocard for Troxilin B3 (BMDB01965)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2006-05-22 15:17:29
Update Date 2009-05-05 20:58:59
Accession Number BMDB01965
Common Name Troxilin B3
Description Troxilin B3 is the enzymatically formed derivative of Hepoxilin B3. 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)
Synonyms
  1. 10,11S,12R-trihydroxy-5Z,8Z,14Z-eicosatrienoic acid
  2. (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acid
  3. (5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid
  4. (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoicacid
  5. (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acid
  6. 10,11S,12R-trihydroxy-5Z,8Z,14Z-eicosatrienoate
  7. (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoate
  8. (5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoate
  9. (5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoate
Chemical IUPAC Name (5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid
Chemical Formula C20H34O5
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Fatty acids
Class
  • Eicosanoids
Sub Class
  • Trihydroxyeicosapolyenoic acids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; 1,2-diol; carboxylic acid; alkene
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 354.481
Monoisotopic Molecular Weight 354.240631
Isomeric SMILES CCCCCC=C/C[C@@H](O)[C@H](O)C(O)C=C/CC=C/CCCC(O)=O
Canonical SMILES CCCCCC=CCC(O)C(O)C(O)C=CCC=CCCCC(O)=O
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 5283210 Link Image
PubChem Substance 14718361 Link Image
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/C20H34O5/c1-2-3-4-5-8-11-14-17(21)20(25)18(22)15-12-9-6-7-10-13-16-19(23)24/h6-8,11-12,15,17-18,20-22,25H,2-5,9-10,13-14,16H2,1H3,(H,23,24)/b7-6-,11-8-,15-12-/t17-,18?,20+/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0521 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 4.2 [Predicted by PubChem via XLOGP]; 4.77 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available