Showing metabocard for 4-oxo-Retinoic acid (BMDB0006285)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:21:15 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0006285
Secondary Accession Numbers
  • BMDB06285
Metabolite Identification
Common Name4-oxo-Retinoic acid
Description4-oxo-Retinoic acid, also known as 4-oxo-retinoic acid or 4-oxo-retinoic acid, 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. 4-oxo-Retinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-oxo-Retinoic acid can be biosynthesized from 4-hydroxyretinoic acid; which is mediated by the enzyme cytochrome P450 26A1. In cattle, 4-oxo-retinoic acid is involved in the metabolic pathway called the retinol metabolism pathway.
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 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-1190000000-91cc9f2a067e55470ee6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4149000000-1c6f86c22c6c874c8d5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0393000000-ee02331a6bc33c74454cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvs-1590000000-8302c918b8678930f190View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mk-6920000000-7c7f25147d9e24da29a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0069000000-d9c525084e53a73b4a7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1096000000-f6a17be3ddcaa73ade82View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6w-4490000000-e09099a374036880e884View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0493000000-dc399cf44f47f04180bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9b-1960000000-d3ac3e8652a2bc6d4a64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kbu-3910000000-9b786cbd709288245f36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0079000000-16a7e691d9676e7c84c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0390000000-afcececf071a831da85eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-3920000000-80cd4fb181bfdfc81346View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
  • Nucleus
Biospecimen Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0006285
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 26B1
General function:
Not Available
Specific function:
Involved in the metabolism of retinoic acid (RA), rendering this classical morphogen inactive through oxidation. Involved in the specific inactivation of all-trans-retinoic acid (all-trans-RA), with a preference for the following substrates: all-trans-RA > 9-cis-RA > 13-cis-RA. Generates several hydroxylated forms of RA, including 4-OH-RA, 4-oxo-RA, and 18-OH-RA. Essential for postnatal survival. Plays a central role in germ cell development: acts by degrading RA in the developing testis, preventing STRA8 expression, thereby leading to delay of meiosis. Required for the maintenance of the undifferentiated state of male germ cells during embryonic development in Sertoli cells, inducing arrest in G0 phase of the cell cycle and preventing meiotic entry. Plays a role in skeletal development, both at the level of patterning and in the ossification of bone and the establishment of some synovial joints (By similarity).
Gene Name:
CYP26B1
Uniprot ID:
E1BHJ4
Molecular weight:
57414.0
Reactions
4-Hydroxyretinoic acid → 4-oxo-Retinoic aciddetails