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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-06-16 13:14:51 UTC
Update Date2019-07-23 05:57:47 UTC
HMDB IDHMDB0012329
Secondary Accession Numbers
  • HMDB12329
Metabolite Identification
Common Name4-Oxoretinol
Description4-oxo-retinol, a metabolite of retinol synthesized in mouse embryonal carcinoma F9 cells,is active in inducing differentiation of these cells. It also functions as a ligand of retinoic acid receptors and a transcriptional activator of reporter. genes.[PMID: 9110564 ]. 4-Oxoretinol is a metabolite of retinol in the human promyelocytic leukemia cell line NB4 which induces cell growth arrest and granulocytic differentiation.[PMID: 9581846 ].
Structure
Data?1563861467
Synonyms
ValueSource
4-KetoretinolChEBI
4-oxo-ROLChEBI
3,7-Dimethyl-9-(3-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-olHMDB
4-Ketovitamin a(1)HMDB
4-Ketovitamin-a-alcoholHMDB
4-Ketovitamin-alpha-alcoholHMDB
4-oxo-RetinolHMDB
4-OxoROLHMDB
4-Oxovitamin a1HMDB
4-Oxovitamin-a-alcoholHMDB
4-Oxovitamin-alpha-alcoholHMDB
4OVA1HMDB
all-trans-4-OxoretinolHMDB
OXRHMDB
Chemical FormulaC20H28O2
Average Molecular Weight300.4351
Monoisotopic Molecular Weight300.20893014
IUPAC Name3-[(1E,3E,5E,7E)-9-hydroxy-3,7-dimethylnona-1,3,5,7-tetraen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one
Traditional Name4-oxoretinol
CAS Registry Number62702-55-0
SMILES
C\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C
InChI Identifier
InChI=1S/C20H28O2/c1-15(7-6-8-16(2)12-14-21)9-10-18-17(3)19(22)11-13-20(18,4)5/h6-10,12,21H,11,13-14H2,1-5H3/b8-6+,10-9+,15-7+,16-12+
InChI KeyPLIUCYCUYQIBDZ-RMWYGNQTSA-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
  • Retinoid skeleton
  • Diterpenoid
  • Fatty alcohol
  • Cyclohexenone
  • Fatty acyl
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.012 g/LALOGPS
logP5.31ALOGPS
logP4.03ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)16.44ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.62 m³·mol⁻¹ChemAxon
Polarizability36.69 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1290000000-4649d7f3ab4f61c01fafJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2129000000-ba7d9fd4931eaf6b6927JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0593000000-fac47a7263b1f70432a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-2960000000-e6ecb0d2ae19b738762bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-8920000000-f526453f90130e118ba0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-c06dba726fc1a33b336fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0090000000-13c1ec01c1d802584537JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frx-3490000000-ca40eaf3790e425d4408JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02699
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028948
KNApSAcK IDNot Available
Chemspider ID4451124
KEGG Compound IDC16683
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5289090
PDB IDOXR
ChEBI ID44597
Food Biomarker OntologyNot Available
VMH IDM01032
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ross SA, De Luca LM: A new metabolite of retinol: all-trans-4-oxo-retinol as a receptor activator and differentiation agent. Nutr Rev. 1996 Nov;54(11 Pt 1):355-6. [PubMed:9110564 ]
  2. Faria TN, Rivi R, Derguini F, Pandolfi PP, Gudas LJ: 4-Oxoretinol, a metabolite of retinol in the human promyelocytic leukemia cell line NB4, induces cell growth arrest and granulocytic differentiation. Cancer Res. 1998 May 1;58(9):2007-13. [PubMed:9581846 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.