Showing metabocard for all-trans-18-Hydroxyretinoic acid (BMDB0012452)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:38:50 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0012452
Secondary Accession Numbers
  • BMDB12452
Metabolite Identification
Common Nameall-trans-18-Hydroxyretinoic acid
Descriptionall-trans-18-Hydroxyretinoic acid, also known as All-trans-18-hydroxyretinoic acid or All-trans-All-trans-all-trans-18-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. all-trans-18-Hydroxyretinoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. all-trans-18-Hydroxyretinoic acid can be biosynthesized from all-trans-retinoic acid through its interaction with the enzyme cytochrome P450 26A1. In cattle, all-trans-All-trans-all-trans-18-hydroxyretinoic acid is involved in the metabolic pathway called the retinol metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
18-Hydroxy-all-trans-retinoic acidChEBI
18-Hydroxyretinoic acidChEBI
all-trans-9-(2-(Hydroxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraenoic acidChEBI
18-Hydroxy-all-trans-retinoateGenerator
18-HydroxyretinoateGenerator
all-trans-9-(2-(Hydroxymethyl)-6,6-dimethyl-1-cyclohexen-1-yl)-3,7-dimethyl-2,4,6,8-nonatetraenoateGenerator
all-trans-18-HydroxyretinoateGenerator
rac-18-Hydroxy-all-trans-retinoateHMDB
rac-18-Hydroxy-all-trans-retinoic acidHMDB
all-trans-18-Hydroxyretinoic acidHMDB
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Traditional Name(2E,4E,6E,8E)-9-[2-(hydroxymethyl)-6,6-dimethylcyclohex-1-en-1-yl]-3,7-dimethylnona-2,4,6,8-tetraenoic acid
CAS Registry Number63531-93-1
SMILES
C\C(\C=C\C1=C(CO)CCCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=1S/C20H28O3/c1-15(7-5-8-16(2)13-19(22)23)10-11-18-17(14-21)9-6-12-20(18,3)4/h5,7-8,10-11,13,21H,6,9,12,14H2,1-4H3,(H,22,23)/b8-5+,11-10+,15-7+,16-13+
InChI KeyXSJOIRFEYHJNAW-FCKHSPHMSA-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
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Primary 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.79ALOGPS
logP3.73ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)5ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity99.57 m³·mol⁻¹ChemAxon
Polarizability37.47 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, Positivesplash10-0uds-1193000000-626f700ca215d387c08aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006t-7207900000-65114d88bd7672d578d7View 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, Positivesplash10-0002-0291000000-333cc246ec7c4b1e0475View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9b-1790000000-a89fdd69531c41151cfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000m-5900000000-9edad0e8ff3f631ee2cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0097000000-18d34b6fd796886621beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-0092000000-92fbb8e3830fc0d48609View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0670-1290000000-b6dfa3839044995ad66bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0097000000-b61c2e80fa56e367a872View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0g4i-0190000000-d269f050ce5c3390aa06View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016r-4890000000-44334e23d3a0de779de8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01bm-0291000000-27b81458a8ba96303e29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00yl-0290000000-ea8b6b5eb2c38cb4c7b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kvo-7900000000-eb24d930d5dbda34997cView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0012452
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029068
KNApSAcK IDNot Available
Chemspider ID5005673
KEGG Compound IDC16679
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6506224
PDB IDNot Available
ChEBI ID80657
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
Retinoic acid → all-trans-18-Hydroxyretinoic aciddetails