4-Oxoretinol (CHEM040787)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:34:07 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040787
Identification
Common Name4-Oxoretinol
ClassSmall Molecule
DescriptionA retinoid that is all-trans-retinol in which the hydrogens at position 4 have been replaced by an oxo group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass300.435 g/mol
Monoisotopic Mass300.209 g/mol
CAS Registry Number62702-55-0
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
SMILESC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1290000000-4649d7f3ab4f61c01fafSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-2129000000-ba7d9fd4931eaf6b6927Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0593000000-fac47a7263b1f70432a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-2960000000-e6ecb0d2ae19b738762bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-8920000000-f526453f90130e118ba0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-c06dba726fc1a33b336fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0090000000-13c1ec01c1d802584537Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frx-3490000000-ca40eaf3790e425d4408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-d04e40563394d4c84f5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066s-0190000000-f4b17a8c6d2a8521525aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0590000000-35e8dfa966822e3e2574Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsr-0792000000-1526d46586ab5fe6ae7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lb-1930000000-c9e30f5fc51a908c8495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-3900000000-eefd04e3e622ffcc6615Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02699
HMDB IDHMDB0012329
FooDB IDFDB028948
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDOXR
Wikipedia LinkNot Available
Chemspider ID4451124
ChEBI ID44597
PubChem Compound ID5289090
Kegg Compound IDC16683
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10415093
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10557354
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15817863
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17943179
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18006143
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=19492420
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24662164
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=8643497
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=9377581
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=9581846
11. 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.
12. 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.
13. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
14. 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.
15. 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.
16. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
17. The lipid handbook with CD-ROM