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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2022-03-07 02:49:11 UTC
HMDB IDHMDB0001965
Secondary Accession Numbers
  • HMDB01965
Metabolite Identification
Common NameTroxilin B3
DescriptionTroxilin 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 ).
Structure
Data?1582752220
Synonyms
ValueSource
(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acidChEBI
(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acidChEBI
10,11S,12R-TriOH all-cis-5,8,14-20:3ChEBI
10,11S,12R-TriOH all-cis-5,8,14-C20:3ChEBI
(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoic acidKegg
(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acidKegg
(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoateGenerator
(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoateGenerator
(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoateGenerator
(5Z,8Z,14Z)-(11R,12R)-10,11,12-Trihydroxyicosa-5,8,14-trienoateGenerator
(5Z,8Z,11S,12R,14Z)-10,11,12-Trihydroxyicosa-5,8,14-trienoateHMDB
(5Z,8Z,11S,12R,14Z)-10,11,12-Trihydroxyicosa-5,8,14-trienoic acidHMDB
(5Z,8Z,14Z)-(11S,12R)-10,11,12-Trihydroxyeicosa-5,8,14-trienoicacidHMDB
10,11S,12R-Trihydroxy-5Z,8Z,14Z-eicosatrienoateHMDB
10,11S,12R-Trihydroxy-5Z,8Z,14Z-eicosatrienoic acidHMDB
TRXB(3)HMDB
Trioxilin b3HMDB
Troxilin b3ChEBI
Chemical FormulaC20H34O5
Average Molecular Weight354.481
Monoisotopic Molecular Weight354.240624198
IUPAC Name(5Z,8Z,11S,12R,14Z)-10,11,12-trihydroxyicosa-5,8,14-trienoic acid
Traditional Nametrioxilin B3
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/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
InChI KeyGOHNIXDAQODZKP-OZPSOFALSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
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

Source

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 Solubility0.052 g/LALOGPS
logP4.76ALOGPS
logP3.57ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity103.08 m³·mol⁻¹ChemAxon
Polarizability40.34 ųChemAxon
Number of Rings0ChemAxon
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]+192.18731661259
DarkChem[M-H]-192.97831661259
AllCCS[M+H]+196.17132859911
AllCCS[M-H]-191.46332859911
DeepCCS[M+H]+200.14930932474
DeepCCS[M-H]-197.46530932474
DeepCCS[M-2H]-232.08230932474
DeepCCS[M+Na]+207.3130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Troxilin B3CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O4443.1Standard polar33892256
Troxilin B3CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O2699.1Standard non polar33892256
Troxilin B3CCCCC\C=C/C[C@@H](O)[C@H](O)C(O)\C=C/C\C=C/CCCC(O)=O2791.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Troxilin B3,1TMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O2847.2Semi standard non polar33892256
Troxilin B3,1TMS,isomer #2CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O2873.8Semi standard non polar33892256
Troxilin B3,1TMS,isomer #3CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2884.1Semi standard non polar33892256
Troxilin B3,1TMS,isomer #4CCCCC/C=C\C[C@@H](O)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2887.0Semi standard non polar33892256
Troxilin B3,2TMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O2822.9Semi standard non polar33892256
Troxilin B3,2TMS,isomer #2CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2859.9Semi standard non polar33892256
Troxilin B3,2TMS,isomer #3CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2820.7Semi standard non polar33892256
Troxilin B3,2TMS,isomer #4CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2874.1Semi standard non polar33892256
Troxilin B3,2TMS,isomer #5CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2834.3Semi standard non polar33892256
Troxilin B3,2TMS,isomer #6CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2842.5Semi standard non polar33892256
Troxilin B3,3TMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C2829.4Semi standard non polar33892256
Troxilin B3,3TMS,isomer #2CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C2758.7Semi standard non polar33892256
Troxilin B3,3TMS,isomer #3CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2809.2Semi standard non polar33892256
Troxilin B3,3TMS,isomer #4CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2812.6Semi standard non polar33892256
Troxilin B3,4TMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2808.6Semi standard non polar33892256
Troxilin B3,1TBDMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O3118.7Semi standard non polar33892256
Troxilin B3,1TBDMS,isomer #2CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O3142.9Semi standard non polar33892256
Troxilin B3,1TBDMS,isomer #3CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3124.6Semi standard non polar33892256
Troxilin B3,1TBDMS,isomer #4CCCCC/C=C\C[C@@H](O)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3160.3Semi standard non polar33892256
Troxilin B3,2TBDMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O3321.6Semi standard non polar33892256
Troxilin B3,2TBDMS,isomer #2CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3326.2Semi standard non polar33892256
Troxilin B3,2TBDMS,isomer #3CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3329.3Semi standard non polar33892256
Troxilin B3,2TBDMS,isomer #4CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3323.4Semi standard non polar33892256
Troxilin B3,2TBDMS,isomer #5CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3335.5Semi standard non polar33892256
Troxilin B3,2TBDMS,isomer #6CCCCC/C=C\C[C@@H](O)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3322.9Semi standard non polar33892256
Troxilin B3,3TBDMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O)O[Si](C)(C)C(C)(C)C3525.0Semi standard non polar33892256
Troxilin B3,3TBDMS,isomer #2CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(O)/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C3519.0Semi standard non polar33892256
Troxilin B3,3TBDMS,isomer #3CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3549.4Semi standard non polar33892256
Troxilin B3,3TBDMS,isomer #4CCCCC/C=C\C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3522.5Semi standard non polar33892256
Troxilin B3,4TBDMS,isomer #1CCCCC/C=C\C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C(/C=C\C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3715.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Troxilin B3 GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1922000000-2486e1dc6b23983b3ce02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxilin B3 GC-MS (4 TMS) - 70eV, Positivesplash10-004i-7316259000-675b32ecc0b9ab74a5ce2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Troxilin B3 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 - Troxilin B3 10V, Positive-QTOFsplash10-052r-0309000000-53c7d7aa045b57801cf92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 20V, Positive-QTOFsplash10-0909-1902000000-e03e31d6b3e5340800ed2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 40V, Positive-QTOFsplash10-052f-9700000000-cc5d7039eb0bf54194b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 10V, Negative-QTOFsplash10-0udi-0519000000-04904b3f12510c6d31d22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 20V, Negative-QTOFsplash10-0v5i-0901000000-038f2e2580c0adcafddc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 40V, Negative-QTOFsplash10-0a4i-9800000000-3c1f9c39c2fcce5815cf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 10V, Positive-QTOFsplash10-05n0-0419000000-fd729f35d159a62d1ac42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 20V, Positive-QTOFsplash10-07bf-9633000000-6106d1c6c5f2017c87452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 40V, Positive-QTOFsplash10-05nf-9500000000-484a1d34f2b84853ec822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 10V, Negative-QTOFsplash10-0udi-0319000000-34e1ea22e79daacffd742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 20V, Negative-QTOFsplash10-0udi-1914000000-a6be2ee239b987299b392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Troxilin B3 40V, Negative-QTOFsplash10-0002-3900000000-bba6b26deed00675ac4c2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022768
KNApSAcK IDNot Available
Chemspider ID4446331
KEGG Compound IDC14811
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283210
PDB IDNot Available
ChEBI ID35032
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. 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 ]