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Human Metabolome Database Version 3.5

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Showing metabocard for 4-oxo-Retinoic acid (HMDB06285)

Record Information
Version 3.5
Creation Date 2007-05-22 15:24:24 -0600
Update Date 2013-02-08 17:14:43 -0700
HMDB ID HMDB06285
Secondary Accession Numbers None
Metabolite Identification
Common Name 4-oxo-Retinoic acid
Description 4-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 Link_out, 7893159 Link_out, 17330217 Link_out, 16778795 Link_out, 17460545 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 4-Keto-Retinoate
  2. 4-Keto-Retinoic acid
  3. 4-Ketoretinoate
  4. 4-Ketoretinoic acid
  5. 4-Oxo-all-trans-retinoate
  6. 4-Oxo-all-trans-retinoic acid
  7. 4-Oxoretinoate
  8. 4-Oxoretinoic acid
  9. 4-Oxotretinoin
  10. All-trans-4-Oxoretinoate
  11. All-trans-4-Oxoretinoic acid
  12. Ro 11-4824
  13. Ro 12-4824
Chemical Formula C20H26O3
Average Molecular Weight 314.4186
Monoisotopic Molecular Weight 314.188194698
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 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
CAS Registry Number 38030-57-8
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 Key GGCUJPCCTQNTJF-FRCNGJHJSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Retinoids
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Branched Fatty Acids
  • Carbocyclic Fatty Acids
  • Organic Compounds
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Cyclohexene
  • Enone
  • Isoprene
  • Ketone
  • Medium Chain Keto Acid
Direct Parent Retinoids
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Nucleus
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0062 g/L ALOGPS
LogP 4.94 ALOGPS
LogP 4.35 ChemAxon
LogS -4.71 ALOGPS
pKa (strongest acidic) 5 ChemAxon
pKa (strongest basic) -4.8 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 54.37 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 98.48 ChemAxon
Polarizability 36.62 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Nucleus
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Retinol Metabolism SMP00074 map00830 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023877
KNApSAcK ID Not Available
Chemspider ID 4941652 Link_out
KEGG Compound ID C16678 Link_out
BioCyc ID Not Available
BiGG ID 2430195 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB06285 Link_out
Metagene Link HMDB06285 Link_out
METLIN ID Not Available
PubChem Compound 6437063 Link_out
PDB ID Not Available
ChEBI ID 269971 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available