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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-06-18 12:13:05 UTC
Update Date2017-10-31 16:15:02 UTC
HMDB IDHMDB0012451
Secondary Accession Numbers
  • HMDB12451
Metabolite Identification
Common Nameall-trans-5,6-Epoxyretinoic acid
DescriptionAll-trans-5,6-epoxyretinoic acid, also known as all-trans-5,6-Epoxy-5,6-dihydroretinoate or 56-Epoxyretinoate, is classified as a member of the retinoids. Retinoids are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. All-trans-5,6-epoxyretinoic acid is considered to be a practically insoluble (in water) and a weak acidic compound. All-trans-5,6-epoxyretinoic acid is an isoprenoid lipid molecule. All-trans-5,6-epoxyretinoic acid can be found primarily in human kidney and liver tissues; and in blood and urine. Within a cell, All-trans-5,6-epoxyretinoic acid is primarily located in the cytoplasm, in the extracellular space or near the membrane.
Structure
Thumb
Synonyms
ValueSource
all-trans-5,6-Epoxy-5,6-dihydroretinoic acidKegg
all-trans-5,6-Epoxy-5,6-dihydroretinoateGenerator
all-trans-5,6-EpoxyretinoateGenerator
5,6-Epoxy-5,6-dihydro-retinoateHMDB
5,6-Epoxy-5,6-dihydro-retinoic acidHMDB
5,6-Epoxyretinoic acid, (13-cis)-isomerMeSH
5,6-Epoxyretinoic acid, sodium saltMeSH
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid
Traditional Name(2E,4E,6E,8E)-3,7-dimethyl-9-{2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}nona-2,4,6,8-tetraenoic acid
CAS Registry NumberNot Available
SMILES
C\C(\C=C\C12OC1(C)CCCC2(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+
InChI KeyKEEHJLBAOLGBJZ-WEDZBJJJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoic acid
  • Diterpenoid
  • Retinoid skeleton
  • Medium-chain fatty acid
  • Branched fatty acid
  • Epoxy fatty acid
  • Heterocyclic fatty acid
  • Oxepane
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Ether
  • Oxacycle
  • Oxirane
  • Dialkyl ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP5.74ALOGPS
logP4.54ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)4.94ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.83 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.52 m³·mol⁻¹ChemAxon
Polarizability37.21 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0gb9-9174000000-06301725f04dbf9da5b0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9126000000-aaab7da3a75ae7d0ac69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-066s-0394000000-5ab9d9f9a6f2942b53feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3490000000-ecf50862a1162e1b0ba8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-801580c3c0c49c76fd08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0179000000-815f6a20a086d254820bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01b9-1195000000-c470ae42b6bb7613d063View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05a9-6960000000-e311a77eab0f7eeff493View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways
NameSMPDB/PathwhizKEGG
Retinol MetabolismPw000164Pw000164 greyscalePw000164 simpleMap00830
Vitamin A DeficiencyPw000210Pw000210 greyscalePw000210 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00454
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB029067
      KNApSAcK IDNot Available
      Chemspider ID4515523
      KEGG Compound IDC16680
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound5363137
      PDB IDNot Available
      ChEBI ID545933
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
      2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
      3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
      4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
      5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.