Showing metabocard for All-trans-13,14-dihydroretinol (BMDB0011618)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-10-03 18:21:47 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0011618
Secondary Accession Numbers
  • BMDB11618
Metabolite Identification
Common NameAll-trans-13,14-dihydroretinol
Descriptionall-trans-13,14-Dihydroretinol 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. Thus, all-trans-All-trans-all-trans-13,14-dihydroretinol is considered to be an isoprenoid lipid molecule. all-trans-13,14-Dihydroretinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. all-trans-13,14-Dihydroretinol exists in all living organisms, ranging from bacteria to humans. all-trans-13,14-Dihydroretinol can be biosynthesized from vitamin a through its interaction with the enzyme all-trans-retinol 13,14-reductase. In cattle, all-trans-All-trans-all-trans-13,14-dihydroretinol is involved in the metabolic pathway called the retinol metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
13,14-DihydroretinolChEBI
13,14-Dihydro-all-trans-retinolHMDB
13,14-Dihydro-retinolHMDB
Chemical FormulaC20H32O
Average Molecular Weight288.4675
Monoisotopic Molecular Weight288.245315646
IUPAC Name(4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-4,6,8-trien-1-ol
Traditional Name13,14-dihydroretinol
CAS Registry Number115797-14-3
SMILES
CC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C
InChI Identifier
InChI=1S/C20H32O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-12,17,21H,7,10,13-15H2,1-5H3/b9-6+,12-11+,16-8+
InChI KeyOVBOQVAIYMSUDT-HRYGCDPOSA-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
  • Retinoid skeleton
  • Diterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • 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
logP6.11ALOGPS
logP4.94ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)17.21ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity97.23 m³·mol⁻¹ChemAxon
Polarizability37.13 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, Positivesplash10-00di-3290000000-50a2d27c4e5b3092828aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-7259000000-c043fe3a5e5f48c88c48View 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, Positivesplash10-0079-1590000000-305f5c3efcc6bbc100d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00s9-4920000000-6a12f345df3ddb86a595View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067r-9710000000-f39cf90bb1534db3c158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f8ae4eefdd8e0d6c6a3cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0090000000-fa8cc05c3e7e51ea73cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-4690000000-a18e2c16a607dab729c0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-3ebe1a43ea8596a21475View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-0190000000-d4dde516c54806fe814dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbc-2950000000-74b22df066dc0c5110aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-1950000000-b7be8f013d56482c890cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-2910000000-343b05ba0dc7811743a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bc-7900000000-5cefb7639e63f6cfeb5aView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011618
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028323
KNApSAcK IDNot Available
Chemspider ID394057
KEGG Compound IDC15492
BioCyc IDCPD-7247
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound446798
PDB IDNot Available
ChEBI ID52075
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Retinol saturase
General function:
Not Available
Specific function:
Not Available
Gene Name:
RETSAT
Uniprot ID:
E1BDK9
Molecular weight:
66777.0
Reactions
Vitamin A + Reduced acceptor → All-trans-13,14-dihydroretinol + Acceptordetails