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Showing Compound 4-Oxoretinol (FDB028948)

Record Information
Version1.0
Creation date2011-09-21 01:47:50 UTC
Update date2015-07-21 06:59:35 UTC
Primary IDFDB028948
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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] [HMDB]
CAS Number62702-55-0
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
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
3,7-dimethyl-9-(3-oxo-2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-olhmdb
4-ketoretinolhmdb
4-ketovitamin A(1)hmdb
4-ketovitamin-A-alcoholhmdb
4-ketovitamin-alpha-alcoholhmdb
4-oxoROLhmdb
4-oxovitamin A1hmdb
4-oxovitamin-A-alcoholhmdb
4-oxovitamin-alpha-alcoholhmdb
all-trans-4-oxoretinolhmdb
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H28O2
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
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
Isomeric SMILESC\C(=C/CO)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)CCC1(C)C
Average Molecular Weight300.4351
Monoisotopic Molecular Weight300.20893014
Classification
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:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Oxoretinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1290000000-4649d7f3ab4f61c01fafSpectrum
Predicted GC-MS4-Oxoretinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4i-2129000000-ba7d9fd4931eaf6b6927Spectrum
Predicted GC-MS4-Oxoretinol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0593000000-fac47a7263b1f70432a32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-2960000000-e6ecb0d2ae19b738762b2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-8920000000-f526453f90130e118ba02017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-c06dba726fc1a33b336f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0090000000-13c1ec01c1d8025845372017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0frx-3490000000-ca40eaf3790e425d44082017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-d04e40563394d4c84f5d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066s-0190000000-f4b17a8c6d2a8521525a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0590000000-35e8dfa966822e3e25742021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fsr-0792000000-1526d46586ab5fe6ae7d2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00lb-1930000000-c9e30f5fc51a908c84952021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-3900000000-eefd04e3e622ffcc66152021-09-24View Spectrum
NMRNot Available
ChemSpider ID4451124
ChEMBL IDNot Available
KEGG Compound IDC16683
Pubchem Compound ID5289090
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02699
HMDB IDHMDB12329
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDOXR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Retinol MetabolismSMP00074 map00830
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference