(5S,6S)-di-HETE (YMDB00728)

Identification
YMDB IDYMDB00728
Name(5S,6S)-di-HETE
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description(5S,6S)-di-HETE, also known as 5S,6S-dihete, belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds. Thus, (5S,6S)-di-hete is considered to be an eicosanoid lipid molecule (5S,6S)-di-HETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (5S,6S,7E,9E,11Z,14Z)-5,6-dihydroxyeicosa-7,9,11,14-tetraenoic acid
  • 15-epi-LXA(,4)
  • 5(S),6(R),15(R)-trihydroxy-7E,9E,11Z,13E-eicosatetraenoate
  • 5S,6S-DiHETE
  • 5S,6S-dihydroxy-7E,9E,11Z,14Z-eicosatetraenoic acid
  • threo-(5S,6S)-dihydroxy-7,9-trans-11,14-cis-eicosatetraenoic acid
  • (5S,6S,7E,9E,11Z,14Z)-5,6-Dihydroxyicosatetraenoic acid
  • (5S,6S,7E,9E,11Z,14Z)-5,6-Dihydroxyeicosa-7,9,11,14-tetraenoate
  • (5S,6S,7E,9E,11Z,14Z)-5,6-Dihydroxyicosatetraenoate
  • 5S,6S-Dihydroxy-7E,9E,11Z,14Z-eicosatetraenoate
  • Threo-(5S,6S)-dihydroxy-7,9-trans-11,14-cis-eicosatetraenoate
CAS numberNot Available
WeightAverage: 336.4657
Monoisotopic: 336.230059512
InChI KeyUVZBUUTTYHTDRR-WAQVJNLQSA-N
InChIInChI=1S/C20H32O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18(21)19(22)16-14-17-20(23)24/h6-7,9-13,15,18-19,21-22H,2-5,8,14,16-17H2,1H3,(H,23,24)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1
IUPAC Name(5S,6S,7E,9E,11Z,14Z)-5,6-dihydroxyicosa-7,9,11,14-tetraenoic acid
Traditional IUPAC Name5S,6S-DiHETE
Chemical FormulaC20H32O4
SMILESCCCCC\C=C/C\C=C/C=C/C=C/[C@H](O)[C@@H](O)CCCC(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroxyl group and four CC double bonds.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentHydroxyeicosatetraenoic acids
Alternative Parents
Substituents
  • Hydroxyeicosatetraenoic acid
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Fatty acid
  • Secondary alcohol
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP5.33ALOGPS
logP4.28ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity102.83 m³·mol⁻¹ChemAxon
Polarizability39.87 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • nucleus
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG Reactions
leukotriene A4 + water ↔ (5S,6S)-di-HETE
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-3493000000-319a30f751e1fc83fa2cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0129000000-f27c45f687705283a75aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000f-8943000000-1bfb4c0b9663acba7c54JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9820000000-7a0a057c4ea8a447411eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0129000000-d0430697e05a66d26030JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-5696000000-66c27c940c4a0b09ece7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9340000000-2f2d8544750dbd71d1bcJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Albuquerque, C. P., Smolka, M. B., Payne, S. H., Bafna, V., Eng, J., Zhou, H. (2008). "A multidimensional chromatography technology for in-depth phosphoproteome analysis." Mol Cell Proteomics 7:1389-1396.18407956
  • Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID53026
HMDB IDNot Available
Pubchem Compound ID5283161
Kegg IDNot Available
ChemSpider ID23255694
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Leukotriene A-4 hydrolase
General function:
Involved in binding
Specific function:
Hydrolyzes an epoxide moiety of LTA(4) to form LTB(4). The enzyme also has aminopeptidase activity
Gene Name:
Not Available
Uniprot ID:
Q10740
Molecular weight:
77352.10156
Reactions
(7E,9E,11Z,14Z)-(5S,6S)-5,6-epoxyicosa-7,9,11,14-tetraenoate + H(2)O → (6Z,8E,10E,14Z)-(5S,12R)-5,12-dihydroxyicosa-6,8,10,14-tetraenoate.