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Record Information
Version4.0
Creation Date2007-05-22 19:40:54 UTC
Update Date2017-09-27 08:24:42 UTC
HMDB IDHMDB0006254
Secondary Accession Numbers
  • HMDB06254
Metabolite Identification
Common Name4-Hydroxyretinoic acid
Description4-Hydroxyretinoic acid is an NADPH-dependent hydroxylation metabolite of retinoic acid in the microsomes, via the cytochrome P-450 system. Retinoic acid is an activated metabolite of retinol that supports the systemic functions of vitamin A in vivo. (PMID: 1538719 , 1932598 , 2851384 ).
Structure
Thumb
Synonyms
ValueSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidChEBI
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acidChEBI
(7E,9E,11E,13E)-4-Hydroxyretinoic acidChEBI
4-Hydroxy-(7E,9E,11E,13E)-retinoic acidChEBI
4-Hydroxy-all-trans-retinoic acidChEBI
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateGenerator
4-HydroxyretinoateGenerator
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoateGenerator
(7E,9E,11E,13E)-4-HydroxyretinoateGenerator
4-Hydroxy-(7E,9E,11E,13E)-retinoateGenerator
4-Hydroxy-all-trans-retinoateGenerator
4-Hydroxy-13-cis-retinoateHMDB
4-Hydroxy-13-cis-retinoic acidHMDB
4-Hydroxy-retinoateHMDB
4-Hydroxy-retinoic acidHMDB
4-OH-RetinoateHMDB
4-OH-Retinoic acidHMDB
all-trans-4-HydroxyretinoateHMDB
all-trans-4-Hydroxyretinoic acidHMDB
rac-4-Hydroxy-all-trans-retinoateHMDB
rac-4-Hydroxy-all-trans-retinoic acidHMDB
4-Hydroxy-13-retinoic acidMeSH
4-Hydroxyretinoic acid, (13-cis)-isomerMeSH
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Traditional Name4-hydroxyretinoic acid
CAS Registry Number66592-72-1
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/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChI KeyKGUMXGDKXYTTEY-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
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

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 Solubility0.009 g/LALOGPS
logP5.04ALOGPS
logP3.78ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.31 m³·mol⁻¹ChemAxon
Polarizability37.33 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, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0292000000-4d5a6c9335a4fa5db05eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg1-0590000000-0b50fabd74e810e935c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pba-3920000000-8958845f26cb19e0194bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableView in JSpectraViewer
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
Displaying all 2 entries
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 IDDBMET00298
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite IDNot Available
      FoodDB IDFDB023862
      KNApSAcK IDNot Available
      Chemspider ID4943093
      KEGG Compound IDC16677
      BioCyc IDNot Available
      BiGG ID2299866
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound6438629
      PDB IDNot Available
      ChEBI ID63795
      References
      Synthesis ReferenceRosenberger, Michael. Retinoic acid metabolites. 1. Total synthesis of 4-hydroxy- and 4-oxoretinoic acid. Journal of Organic Chemistry (1982), 47(9), 1698-701.
      Material Safety Data Sheet (MSDS)Not Available
      General References
      1. Napoli JL, Posch KP, Fiorella PD, Boerman MH: Physiological occurrence, biosynthesis and metabolism of retinoic acid: evidence for roles of cellular retinol-binding protein (CRBP) and cellular retinoic acid-binding protein (CRABP) in the pathway of retinoic acid homeostasis. Biomed Pharmacother. 1991;45(4-5):131-43. [PubMed:1932598 ]
      2. Roberts ES, Vaz AD, Coon MJ: Role of isozymes of rabbit microsomal cytochrome P-450 in the metabolism of retinoic acid, retinol, and retinal. Mol Pharmacol. 1992 Feb;41(2):427-33. [PubMed:1538719 ]
      3. Spear PA, Garcin H, Narbonne JF: Increased retinoic acid metabolism following 3,3',4,4',5,5'-hexabromobiphenyl injection. Can J Physiol Pharmacol. 1988 Sep;66(9):1181-6. [PubMed:2851384 ]