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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-06-16 13:14:51 UTC
Update Date2022-03-07 02:51:23 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?1582753042
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, ChEBI
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

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 Solubility0.012 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+187.79830932474
DeepCCS[M-H]-185.13430932474
DeepCCS[M-2H]-219.73230932474
DeepCCS[M+Na]+194.95930932474
AllCCS[M+H]+176.832859911
AllCCS[M+H-H2O]+173.632859911
AllCCS[M+NH4]+179.732859911
AllCCS[M+Na]+180.532859911
AllCCS[M-H]-181.132859911
AllCCS[M+Na-2H]-181.832859911
AllCCS[M+HCOO]-182.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-OxoretinolC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C3684.1Standard polar33892256
4-OxoretinolC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C2644.0Standard non polar33892256
4-OxoretinolC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C2721.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Oxoretinol,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CCC1=O2742.7Semi standard non polar33892256
4-Oxoretinol,1TMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CC=C1O[Si](C)(C)C2706.6Semi standard non polar33892256
4-Oxoretinol,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C2771.7Semi standard non polar33892256
4-Oxoretinol,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C2563.6Standard non polar33892256
4-Oxoretinol,2TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C2709.7Standard polar33892256
4-Oxoretinol,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CCC1=O2937.6Semi standard non polar33892256
4-Oxoretinol,1TBDMS,isomer #2CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C2917.7Semi standard non polar33892256
4-Oxoretinol,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C3219.4Semi standard non polar33892256
4-Oxoretinol,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C2956.5Standard non polar33892256
4-Oxoretinol,2TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)=C/CO[Si](C)(C)C(C)(C)C)C(C)(C)CC=C1O[Si](C)(C)C(C)(C)C2911.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Oxoretinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1290000000-4649d7f3ab4f61c01faf2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Oxoretinol GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2129000000-ba7d9fd4931eaf6b69272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Oxoretinol 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-Oxoretinol 10V, Positive-QTOFsplash10-0f89-0593000000-fac47a7263b1f70432a32017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Positive-QTOFsplash10-0f7k-2960000000-e6ecb0d2ae19b738762b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Positive-QTOFsplash10-1000-8920000000-f526453f90130e118ba02017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Negative-QTOFsplash10-0002-0090000000-c06dba726fc1a33b336f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Negative-QTOFsplash10-014j-0090000000-13c1ec01c1d8025845372017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Negative-QTOFsplash10-0frx-3490000000-ca40eaf3790e425d44082017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Negative-QTOFsplash10-014i-0090000000-d04e40563394d4c84f5d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Negative-QTOFsplash10-066s-0190000000-f4b17a8c6d2a8521525a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Negative-QTOFsplash10-0udi-0590000000-35e8dfa966822e3e25742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 10V, Positive-QTOFsplash10-0fsr-0792000000-1526d46586ab5fe6ae7d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 20V, Positive-QTOFsplash10-00lb-1930000000-c9e30f5fc51a908c84952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Oxoretinol 40V, Positive-QTOFsplash10-002f-3900000000-eefd04e3e622ffcc66152021-09-24Wishart LabView Spectrum
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
FooDB 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
MarkerDB IDNot Available
Good Scents IDNot Available
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.