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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 19:40:54 UTC
Update Date2021-09-14 15:47:52 UTC
HMDB IDHMDB0006254
Secondary Accession Numbers
  • HMDB06254
Metabolite Identification
Common Name4-Hydroxyretinoic acid
Description4-Hydroxyretinoic acid belongs to the class of organic compounds 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. Based on a literature review a significant number of articles have been published on 4-Hydroxyretinoic acid.
Structure
Data?1582752377
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
(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-HydroxyretinoateGenerator
4-Hydroxy-13-cis-retinoateHMDB
4-Hydroxy-13-cis-retinoic acidHMDB, MeSH
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, HMDB
4-Hydroxyretinoic acid, (13-cis)-isomerMeSH, HMDB
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
Description Belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
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

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP5.04ALOGPS
logP3.78ChemAxon
logS-4.6ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.13631661259
DarkChem[M-H]-180.90831661259
DeepCCS[M+H]+199.98630932474
DeepCCS[M-H]-197.24930932474
DeepCCS[M-2H]-231.92130932474
DeepCCS[M+Na]+207.44630932474
AllCCS[M+H]+181.632859911
AllCCS[M+H-H2O]+178.532859911
AllCCS[M+NH4]+184.432859911
AllCCS[M+Na]+185.232859911
AllCCS[M-H]-183.932859911
AllCCS[M+Na-2H]-184.632859911
AllCCS[M+HCOO]-185.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxyretinoic acidC\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O4116.3Standard polar33892256
4-Hydroxyretinoic acidC\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O2615.3Standard non polar33892256
4-Hydroxyretinoic acidC\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O2730.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxyretinoic acid,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1O[Si](C)(C)C2807.1Semi standard non polar33892256
4-Hydroxyretinoic acid,1TMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C)C(C)(C)CCC1O2841.2Semi standard non polar33892256
4-Hydroxyretinoic acid,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C)C(C)(C)CCC1O[Si](C)(C)C2814.1Semi standard non polar33892256
4-Hydroxyretinoic acid,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1O[Si](C)(C)C(C)(C)C3038.8Semi standard non polar33892256
4-Hydroxyretinoic acid,1TBDMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1O3059.5Semi standard non polar33892256
4-Hydroxyretinoic acid,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)CCC1O[Si](C)(C)C(C)(C)C3254.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyretinoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k92-1093000000-7f88a5d83645fa2a79e92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyretinoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-0092-5008900000-f94c9a4b723e495dbc222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyretinoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxyretinoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 10V, Positive-QTOFsplash10-00kb-0292000000-4d5a6c9335a4fa5db05e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Positive-QTOFsplash10-0zg1-0590000000-0b50fabd74e810e935c02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Positive-QTOFsplash10-0pba-3920000000-8958845f26cb19e0194b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 10V, Negative-QTOFsplash10-014i-0089000000-cdb17ed778c9480eb63e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Negative-QTOFsplash10-0gi1-0094000000-b75b3689212cfa9472cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Negative-QTOFsplash10-0a4i-4390000000-5614482c4d64bf67afaf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 10V, Positive-QTOFsplash10-000t-0291000000-7a67cccc8b73d68d76e32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Positive-QTOFsplash10-0f8i-0490000000-891d9992953ed919a7c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Positive-QTOFsplash10-000l-5920000000-8f663f06367ea569c02e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 10V, Negative-QTOFsplash10-014i-0096000000-123a0c931fe8f0c0d4012021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 20V, Negative-QTOFsplash10-0udi-0190000000-3eec1ef4274b19e5f5372021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxyretinoic acid 40V, Negative-QTOFsplash10-016r-4910000000-9e73ac1032f900dd901d2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Nucleus
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDCE2956
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]