You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 21:24:24 UTC
Update Date2020-02-26 21:26:19 UTC
HMDB IDHMDB0006285
Secondary Accession Numbers
  • HMDB06285
Metabolite Identification
Common Name4-oxo-Retinoic acid
Description4-oxo-Retinoic acid is a biologically active geometric isomer of retinoic acid (RA). 4-oxo-retinoic acid is generated from its precursor canthaxanthin and enhances gap junctional communication in cells. Metabolic transformation of all-trans RA to 4-hydroxylated RA appears to be primarily catalyzed by the cytochrome P 450 (CYP) 26AI in human skin cells. Cellular levels of all-trans RA are meticulously regulated utilizing an array of systems to balance uptake, biosynthesis, catabolism, and efflux transport. RA is a critical regulator of gene expression during embryonic development and in the maintenance of adult epithelial tissues. (PMID: 8794203 , 7893159 , 17330217 , 16778795 , 17460545 ).
Structure
Data?1582752379
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 Weight314.4186
Monoisotopic Molecular Weight314.188194698
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
CAS Registry Number38030-57-8
SMILES
C\C(\C=C\C1=C(C)C(=O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-oxo-Retinoic acid,1TMS,#12814.873https://arxiv.org/abs/1905.12712
4-oxo-Retinoic acid,1TMS,#22843.7876https://arxiv.org/abs/1905.12712
4-oxo-Retinoic acid,1TBDMS,#13036.4434https://arxiv.org/abs/1905.12712
4-oxo-Retinoic acid,1TBDMS,#23079.5723https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1190000000-91cc9f2a067e55470ee62017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4149000000-1c6f86c22c6c874c8d5e2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0393000000-ee02331a6bc33c74454c2016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvs-1590000000-8302c918b8678930f1902016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-6920000000-7c7f25147d9e24da29a62016-06-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0069000000-d9c525084e53a73b4a7c2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1096000000-f6a17be3ddcaa73ade822016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6w-4490000000-e09099a374036880e8842016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Nucleus
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023877
KNApSAcK IDNot Available
Chemspider ID4941652
KEGG Compound IDC16678
BioCyc IDNot Available
BiGG ID2430195
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6437063
PDB IDNot Available
ChEBI ID80656
Food Biomarker OntologyNot Available
VMH IDCE2954
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:8794203 ]
  2. 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. [PubMed:7893159 ]
  3. 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. [PubMed:17330217 ]
  4. 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. [PubMed:16778795 ]
  5. 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. [PubMed:17460545 ]