Showing metabocard for 6-trans-Leukotriene B4 (BMDB0005087)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:15:21 UTC
Update Date2020-05-21 16:27:00 UTC
BMDB IDBMDB0005087
Secondary Accession Numbers
  • BMDB05087
Metabolite Identification
Common Name6-trans-Leukotriene B4
Description6-trans-Leukotriene B4, also known as 6-trans-LTB4 or (6E,5S,12R)-leukotriene B4, belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. Thus, 6-trans-leukotriene B4 is considered to be an eicosanoid. Based on a literature review a significant number of articles have been published on 6-trans-Leukotriene B4.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(5S,6E,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoic acidChEBI
(6E,5S,12R)-Leukotriene b4ChEBI
5(S),12(R)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoic acidChEBI
5S,12R-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acidChEBI
5S,12R-Dihydroxy-6E,8E,10E,14Z-icosatetraenoic acidChEBI
6-trans-LTB4ChEBI
Delta(6)-trans-Leukotriene b4ChEBI
Delta(6)-trans-LT b4ChEBI
(5S,6E,8E,10E,12R,14Z)-5,12-Dihydroxyeicosa-6,8,10,14-tetraenoateGenerator
5(S),12(R)-Dihydroxy-6,8,10,14-(trans,trans,trans,cis)-eicosatetraenoateGenerator
5S,12R-Dihydroxy-6E,8E,10E,14Z-eicosatetraenoateGenerator
5S,12R-Dihydroxy-6E,8E,10E,14Z-icosatetraenoateGenerator
Δ(6)-trans-leukotriene b4Generator
Δ(6)-trans-LT b4Generator
D6-trans-Leukotriene b4HMDB
D6-trans-LTB4HMDB
[S-[R*,s*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoateHMDB
[S-[R*,s*-(e,e,e,Z)]]-5,12-dihydroxy-6,8,10,14-eicosatetraenoic acidHMDB
delta6-trans-LTB4HMDB
delta6-trans-Leukotriene b4HMDB
Δ6-trans-LTB4HMDB
Δ6-trans-leukotriene b4HMDB
5,12-HETEMeSH
5,12-DiHETEMeSH
Leukotriene b-4MeSH
Leukotriene b4MeSH
5,12 HETEMeSH
5,12 DiHETEMeSH
b-4, LeukotrieneMeSH
Leukotrienes bMeSH
LTB4MeSH
Leukotriene bMeSH
Leukotriene b 4MeSH
6-trans-Leukotriene B4HMDB
Chemical FormulaC20H32O4
Average Molecular Weight336.4657
Monoisotopic Molecular Weight336.230059512
IUPAC Name(5S,6E,8E,10E,12R,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid
Traditional Name6-trans-LTB4
CAS Registry Number71652-82-9
SMILES
CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C\[C@@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11+/t18-,19-/m1/s1
InChI KeyVNYSSYRCGWBHLG-UKNWISKWSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentLeukotrienes
Alternative Parents
Substituents
  • Leukotriene
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP3.58Not Available
Predicted Properties
PropertyValueSource
logP5.46ALOGPS
logP4.13ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.65ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.98 m³·mol⁻¹ChemAxon
Polarizability40.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-066r-7896000000-782d01776a33cc451555View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-01rl-9113530000-205b0d713aeb42a9afc2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-000i-0419000000-061132d646cd5dd85a1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-00ks-0829000000-7da7ab59ee0d4812767bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0002-0933000000-3fb381ce0f3609a90222View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-0931000000-ccfdaa3226146fe9edc3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0udj-1940000000-ef988be204f5c54f4b21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0r00-1910000000-e16cc958487f06dc4287View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0006-6900000000-a356f0334bf220eb54ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-052f-9700000000-66a6a217eba63b4874d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QIT , negativesplash10-0a4l-7900000000-aeb350579ea4a84117d0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0619000000-dc49d3f4ab097db18f18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0019000000-69c64ad7b55da6a633e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v4i-5598000000-0a1483f60114546ce2c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9550000000-0ad5f1d400a5ff275f25View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-0029000000-0164a507a03180713a2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-2269000000-52f6b9d4ecc4e26ff1feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9340000000-c2e72464c072384447e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0019000000-bbfb0bde6a04ea9b05bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3439000000-d8140c418a63ad2159a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-9320000000-afb563cb7a2b51e02836View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-74962f74765b30de04acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-3659000000-98607094f1fa036e16e2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5191000000-91a6c7d4dfff9bd70967View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005087
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022416
KNApSAcK IDNot Available
Chemspider ID4446252
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeukotriene B4
METLIN IDNot Available
PubChem Compound5283128
PDB IDNot Available
ChEBI ID63981
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A28
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A28
Uniprot ID:
P79102
Molecular weight:
58152.0
Reactions
6-trans-Leukotriene B4 + NADPH + Oxygen → 20-Hydroxy-leukotriene B4 + NADP + Waterdetails
Enzyme Details
2. Leukotriene A-4 hydrolase
General function:
Amino acid transport and metabolism
Specific function:
Epoxide hydrolase that catalyzes the final step in the biosynthesis of the proinflammatory mediator leukotriene B4. Has also aminopeptidase activity (By similarity).
Gene Name:
LTA4H
Uniprot ID:
Q3SZH7
Molecular weight:
69306.0
Reactions
Leukotriene A4 + Water → 6-trans-Leukotriene B4details