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Showing Compound 4-Oxo-13-cis-retinoate (FDB029175)

Record Information
Version1.0
Creation date2011-09-21 01:51:14 UTC
Update date2015-07-21 06:59:39 UTC
Primary IDFDB029175
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Oxo-13-cis-retinoate
Description4-oxo-9-cis retinoic acid (4-oxo-9cRA) is identified as a major plasma metabolite of 9-cis retinoic acid. Plasma levels of 4-oxo-9-cRA were initially 71% of those of 9cRA, but in contrast to 9cRA, there was no decline in plasma levels.Despite a decline in plasma levels of 9cRA over time, levels of the 4-oxo metabolite tended to persist. While the 4-oxo metabolite is less potent than the parent compound [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP4.83ALOGPS
logP4.35ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-7.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.48 m³·mol⁻¹ChemAxon
Polarizability36.57 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H26O3
IUPAC name(2Z,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-5-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
InChI IdentifierInChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-11-17-16(3)10-12-18(21)20(17,4)5/h6-9,11,13H,10,12H2,1-5H3,(H,22,23)/b8-6+,11-9+,14-7+,15-13-
InChI KeyYOFBBAJVETYSCH-IWRFDTMXSA-N
Isomeric SMILESC\C(\C=C\C1=C(C)CCC(=O)C1(C)C)=C/C=C/C(/C)=C\C(O)=O
Average Molecular Weight314.4186
Monoisotopic Molecular Weight314.188194698
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
  • Retinoic acid
  • Diterpenoid
  • Retinoid skeleton
  • Medium-chain fatty acid
  • Cyclohexenone
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Cyclic ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-Oxo-13-cis-retinoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-2090000000-1c5451b849e980e311b0Spectrum
Predicted GC-MS4-Oxo-13-cis-retinoate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-3029000000-b04d7c59fc3ce4973812Spectrum
Predicted GC-MS4-Oxo-13-cis-retinoate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0391000000-8caaf7c4c017bddfdaa62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1980000000-af3a5fdeff98e8840ec42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbk-4910000000-1506f3079c815eac12262017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0089000000-7665fb8471756952e98c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ta-0094000000-c917b32286fab5a78c612017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxv-6290000000-55b32ed2f34d92f67cfa2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0079000000-16a7e691d9676e7c84c52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0290000000-83e5e9702daddae492f72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-4910000000-e94b1001e037759106b02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0392000000-83a2fc1baaa988e42e552021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbj-0490000000-53eac69477af49e3a40d2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-4910000000-14c7b29334f7c81387472021-09-25View Spectrum
NMRNot Available
ChemSpider ID8171361
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9995780
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12789
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
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
No data available in table
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Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference