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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:24:24 UTC
Update Date2017-10-23 19:04:20 UTC
HMDB IDHMDB0006285
Secondary Accession Numbers
  • HMDB06285
Metabolite Identification
Common Name4-oxo-Retinoic acid
Description4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203 , 7893159 , 17330217 , 16778795 , 17460545 ).
Structure
Thumb
Synonyms
ValueSource
4-keto-RetinoateHMDB
4-keto-Retinoic acidHMDB
4-KetoretinoateHMDB
4-Ketoretinoic acidHMDB
4-oxo-all-trans-RetinoateHMDB
4-oxo-all-trans-Retinoic acidHMDB
4-OxoretinoateHMDB
4-Oxoretinoic acidHMDB
4-OxotretinoinHMDB
all-trans-4-OxoretinoateHMDB
all-trans-4-Oxoretinoic acidHMDB
ro 11-4824HMDB
ro 12-4824HMDB
4-oxo-13-cis-Retinoic acidMeSH
4-oxo-IsotretinoinMeSH
4-oxo-trans-Retinoic acidMeSH
4-Oxoretinoic acid, (13-cis)-isomerMeSH
Chemical FormulaC20H26O3
Average Molecular Weight314.4186
Monoisotopic Molecular Weight314.188194698
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Name4-oxo-retinoic acid
CAS Registry Number38030-57-8
SMILES
C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChI KeyGGCUJPCCTQNTJF-FRCNGJHJSA-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
  • Cyclohexenone
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic 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 Solubility0.0062 g/LALOGPS
logP4.94ALOGPS
logP4.35ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.48 m³·mol⁻¹ChemAxon
Polarizability36.62 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0002-1190000000-91cc9f2a067e55470ee6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4149000000-1c6f86c22c6c874c8d5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0393000000-ee02331a6bc33c74454cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvs-1590000000-8302c918b8678930f190View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-6920000000-7c7f25147d9e24da29a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0069000000-d9c525084e53a73b4a7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1096000000-f6a17be3ddcaa73ade82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6w-4490000000-e09099a374036880e884View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Nucleus
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 IDDBMET00455
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB023877
      KNApSAcK IDNot Available
      Chemspider ID4941652
      KEGG Compound IDC16678
      BioCyc IDNot Available
      BiGG ID2430195
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound6437063
      PDB IDNot Available
      ChEBI ID269971
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Download (PDF)
      General References
      1. Stahl W, Hanusch M, Sies H: 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in 10T1/2 cells. Adv Exp Med Biol. 1996;387:121-8. [PubMed:8794203 ]
      2. Hanusch M, Stahl W, Schulz WA, Sies H: Induction of gap junctional communication by 4-oxoretinoic acid generated from its precursor canthaxanthin. Arch Biochem Biophys. 1995 Mar 10;317(2):423-8. [PubMed:7893159 ]
      3. Gundersen TE, Bastani NE, Blomhoff R: Quantitative high-throughput determination of endogenous retinoids in human plasma using triple-stage liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(7):1176-86. [PubMed:17330217 ]
      4. Heise R, Mey J, Neis MM, Marquardt Y, Joussen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR, Merk HF, Baron JM: Skin retinoid concentrations are modulated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol. 2006 Nov;126(11):2473-80. Epub 2006 Jun 15. [PubMed:16778795 ]
      5. Lee SJ, Perera L, Coulter SJ, Mohrenweiser HW, Jetten A, Goldstein JA: The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans retinoic acid and their assessment in a recombinant cDNA expression system. Pharmacogenet Genomics. 2007 Mar;17(3):169-80. [PubMed:17460545 ]