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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-29 15:47:32 UTC
Update Date2022-03-07 02:51:12 UTC
HMDB IDHMDB0011618
Secondary Accession Numbers
  • HMDB11618
Metabolite Identification
Common NameAll-trans-13,14-dihydroretinol
DescriptionAll-trans-13,14-dihydroretinol, also known as 13,14-dihydro-all-trans-retinol, 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-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.
Structure
Data?1582752929
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
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0063 g/LALOGPS
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 RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.37731661259
DarkChem[M-H]-173.07131661259
DeepCCS[M+H]+179.14930932474
DeepCCS[M-H]-176.79130932474
DeepCCS[M-2H]-209.67730932474
DeepCCS[M+Na]+185.24330932474
AllCCS[M+H]+175.832859911
AllCCS[M+H-H2O]+172.732859911
AllCCS[M+NH4]+178.832859911
AllCCS[M+Na]+179.632859911
AllCCS[M-H]-181.032859911
AllCCS[M+Na-2H]-182.032859911
AllCCS[M+HCOO]-183.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
All-trans-13,14-dihydroretinolCC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C3041.8Standard polar33892256
All-trans-13,14-dihydroretinolCC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C2314.8Standard non polar33892256
All-trans-13,14-dihydroretinolCC(CCO)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C2330.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
All-trans-13,14-dihydroretinol,1TMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)CCO[Si](C)(C)C)C(C)(C)CCC12431.9Semi standard non polar33892256
All-trans-13,14-dihydroretinol,1TBDMS,isomer #1CC1=C(/C=C/C(C)=C/C=C/C(C)CCO[Si](C)(C)C(C)(C)C)C(C)(C)CCC12657.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - All-trans-13,14-dihydroretinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-3290000000-50a2d27c4e5b3092828a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - All-trans-13,14-dihydroretinol GC-MS (1 TMS) - 70eV, Positivesplash10-0002-7259000000-c043fe3a5e5f48c88c482017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - All-trans-13,14-dihydroretinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 10V, Positive-QTOFsplash10-0079-1590000000-305f5c3efcc6bbc100d72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 20V, Positive-QTOFsplash10-00s9-4920000000-6a12f345df3ddb86a5952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 40V, Positive-QTOFsplash10-067r-9710000000-f39cf90bb1534db3c1582017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 10V, Negative-QTOFsplash10-000i-0090000000-f8ae4eefdd8e0d6c6a3c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 20V, Negative-QTOFsplash10-0a4r-0090000000-fa8cc05c3e7e51ea73cb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 40V, Negative-QTOFsplash10-006x-4690000000-a18e2c16a607dab729c02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 10V, Negative-QTOFsplash10-000i-0090000000-3ebe1a43ea8596a214752021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 20V, Negative-QTOFsplash10-0a4r-0190000000-d4dde516c54806fe814d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 40V, Negative-QTOFsplash10-0gbc-2950000000-74b22df066dc0c5110ae2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 10V, Positive-QTOFsplash10-00dr-1950000000-b7be8f013d56482c890c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 20V, Positive-QTOFsplash10-0079-2910000000-343b05ba0dc7811743a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - All-trans-13,14-dihydroretinol 40V, Positive-QTOFsplash10-01bc-7900000000-5cefb7639e63f6cfeb5a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in electron carrier activity
Specific function:
Retinol saturase carrying out the saturation of the 13-14 double bond of all-trans-retinol to produce all-trans-13,14-dihydroretinol. Has activity toward all-trans-retinol as substrate. Does not use all-trans-retinoic acid nor 9-cis, 11-cis or 13-cis-retinol isomers as substrates. May play a role in the metabolism of vitamin A (By similarity).
Gene Name:
RETSAT
Uniprot ID:
Q6NUM9
Molecular weight:
66818.935
Reactions
All-trans-13,14-dihydroretinol + acceptor → Vitamin A + reduced acceptordetails
All-trans-13,14-dihydroretinol + Acceptor → Vitamin A + Reduced acceptordetails