Showing metabocard for 4-Hydroxyretinoic acid (BMDB0006254)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:20:55 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0006254
Secondary Accession Numbers
  • BMDB06254
Metabolite Identification
Common Name4-Hydroxyretinoic acid
Description4-Hydroxyretinoic 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-Hydroxyretinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Hydroxyretinoic acid participates in a number of enzymatic reactions, within cattle. In particular, 4-Hydroxyretinoic acid can be biosynthesized from all-trans-retinoic acid; which is catalyzed by the enzyme cytochrome P450 26A1. In addition, 4-Hydroxyretinoic acid can be converted into 4-oxo-retinoic acid; which is mediated by the enzyme cytochrome P450 26A1. In cattle, 4-hydroxyretinoic acid is involved in the metabolic pathway called the retinol metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acidChEBI
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic acidChEBI
(7E,9E,11E,13E)-4-Hydroxyretinoic acidChEBI
4-Hydroxy-(7E,9E,11E,13E)-retinoic acidChEBI
4-Hydroxy-all-trans-retinoic acidChEBI
(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-3-hydroxy-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoateGenerator
(2E,4E,6E,8E)-9-(3-Hydroxy-2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoateGenerator
(7E,9E,11E,13E)-4-HydroxyretinoateGenerator
4-Hydroxy-(7E,9E,11E,13E)-retinoateGenerator
4-Hydroxy-all-trans-retinoateGenerator
4-HydroxyretinoateGenerator
4-Hydroxy-13-cis-retinoateHMDB
4-Hydroxy-13-cis-retinoic acidHMDB, MeSH
4-Hydroxy-retinoateHMDB
4-Hydroxy-retinoic acidHMDB
4-OH-RetinoateHMDB
4-OH-Retinoic acidHMDB
all-trans-4-HydroxyretinoateHMDB
all-trans-4-Hydroxyretinoic acidHMDB
rac-4-Hydroxy-all-trans-retinoateHMDB
rac-4-Hydroxy-all-trans-retinoic acidHMDB
4-Hydroxy-13-retinoic acidMeSH, HMDB
4-Hydroxyretinoic acid, (13-cis)-isomerMeSH, HMDB
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Traditional Name4-hydroxyretinoic acid
CAS Registry Number66592-72-1
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/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChI KeyKGUMXGDKXYTTEY-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
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • 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
logP5.04ALOGPS
logP3.78ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity99.31 m³·mol⁻¹ChemAxon
Polarizability37.33 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, Positivesplash10-0k92-1093000000-7f88a5d83645fa2a79e9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0092-5008900000-f94c9a4b723e495dbc22View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0292000000-4d5a6c9335a4fa5db05eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zg1-0590000000-0b50fabd74e810e935c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pba-3920000000-8958845f26cb19e0194bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0089000000-cdb17ed778c9480eb63eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gi1-0094000000-b75b3689212cfa9472cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4390000000-5614482c4d64bf67afafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0291000000-7a67cccc8b73d68d76e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f8i-0490000000-891d9992953ed919a7c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-5920000000-8f663f06367ea569c02eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0096000000-123a0c931fe8f0c0d401View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0190000000-3eec1ef4274b19e5f537View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-4910000000-9e73ac1032f900dd901dView 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 IDHMDB0006254
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023862
KNApSAcK IDNot Available
Chemspider ID4943093
KEGG Compound IDC16677
BioCyc IDNot Available
BiGG ID2299866
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438629
PDB IDNot Available
ChEBI ID63795
References
Synthesis ReferenceRosenberger, Michael. Retinoic acid metabolites. 1. Total synthesis of 4-hydroxy- and 4-oxoretinoic acid. Journal of Organic Chemistry (1982), 47(9), 1698-701.
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
Retinoic acid → 4-Hydroxyretinoic aciddetails
4-Hydroxyretinoic acid → 4-oxo-Retinoic aciddetails