4-oxo-Retinoic acid (CHEM022722)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:48:57 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022722
Identification
Common Name4-oxo-Retinoic acid
ClassSmall Molecule
DescriptionA retinoid that consists of all-trans-retinoic acid bearing an oxo substituent at position 4 on the cyclohexenyl ring.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-oxo-all-trans-Retinoic acidChEBI
4-oxo-AtRAChEBI
4-oxo-all-trans-RetinoateGenerator
4-oxo-RetinoateGenerator
4-keto-RetinoateHMDB
4-keto-Retinoic acidHMDB
4-KetoretinoateHMDB
4-Ketoretinoic acidHMDB, MeSH
4-OxoretinoateHMDB
4-Oxoretinoic acidHMDB, MeSH
4-OxotretinoinHMDB
all-trans-4-OxoretinoateHMDB
all-trans-4-Oxoretinoic acidHMDB
ro 11-4824HMDB
ro 12-4824HMDB
4-oxo-13-cis-Retinoic acidMeSH, HMDB
4-oxo-IsotretinoinMeSH, HMDB
4-oxo-trans-Retinoic acidMeSH, HMDB
4-Oxoretinoic acid, (13-cis)-isomerMeSH, HMDB
Chemical FormulaC20H26O3
Average Molecular Mass314.419 g/mol
Monoisotopic Mass314.188 g/mol
CAS Registry Number38030-57-8
IUPAC Name(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Traditional Name4-oxo-retinoic acid
SMILESC\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI IdentifierInChI=1S/C20H26O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChI KeyGGCUJPCCTQNTJF-FRCNGJHJSA-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
  • 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 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 Solubility0.0062 g/LALOGPS
logP4.94ALOGPS
logP4.35ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity98.48 m³·mol⁻¹ChemAxon
Polarizability36.62 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1190000000-91cc9f2a067e55470ee6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4149000000-1c6f86c22c6c874c8d5eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0393000000-ee02331a6bc33c74454cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvs-1590000000-8302c918b8678930f190Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-6920000000-7c7f25147d9e24da29a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0069000000-d9c525084e53a73b4a7cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1096000000-f6a17be3ddcaa73ade82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6w-4490000000-e09099a374036880e884Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0493000000-dc399cf44f47f04180bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9b-1960000000-d3ac3e8652a2bc6d4a64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbu-3910000000-9b786cbd709288245f36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0079000000-16a7e691d9676e7c84c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0390000000-afcececf071a831da85eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-3920000000-80cd4fb181bfdfc81346Spectrum
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 IDNot Available
HMDB IDHMDB0006285
FooDB IDFDB023877
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2430195
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4941652
ChEBI ID80656
PubChem Compound ID6437063
Kegg Compound IDC16678
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=2051220
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25492813
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2772923
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=435468
5. Stahl W, Hanusch M, Sies H: 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in 10T1/2 cells. Adv Exp Med Biol. 1996;387:121-8.
6. Hanusch M, Stahl W, Schulz WA, Sies H: Induction of gap junctional communication by 4-oxoretinoic acid generated from its precursor canthaxanthin. Arch Biochem Biophys. 1995 Mar 10;317(2):423-8.
7. Gundersen TE, Bastani NE, Blomhoff R: Quantitative high-throughput determination of endogenous retinoids in human plasma using triple-stage liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(7):1176-86.
8. Heise R, Mey J, Neis MM, Marquardt Y, Joussen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR, Merk HF, Baron JM: Skin retinoid concentrations are modulated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol. 2006 Nov;126(11):2473-80. Epub 2006 Jun 15.
9. Lee SJ, Perera L, Coulter SJ, Mohrenweiser HW, Jetten A, Goldstein JA: The discovery of new coding alleles of human CYP26A1 that are potentially defective in the metabolism of all-trans retinoic acid and their assessment in a recombinant cDNA expression system. Pharmacogenet Genomics. 2007 Mar;17(3):169-80.