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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-21 06:25:53 UTC
Update Date2019-07-23 07:18:33 UTC
HMDB IDHMDB0062447
Secondary Accession Numbers
  • HMDB62447
Metabolite Identification
Common Nameanhydroretinol
Descriptionanhydroretinol, also known as anhydrovitamin a, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. anhydroretinol is possibly neutral.
Structure
Data?1563866313
Synonyms
ValueSource
Anhydrovitamin aHMDB
trans-Anhydrovitamin aHMDB
AnhydroretinolMeSH
Chemical FormulaC20H28
Average Molecular Weight268.4363
Monoisotopic Molecular Weight268.219100896
IUPAC Name(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraen-1-ylidene]-1,5,5-trimethylcyclohex-1-ene
Traditional Name(6E)-6-[(2E,4E,6E)-3,7-dimethylnona-2,4,6,8-tetraen-1-ylidene]-1,5,5-trimethylcyclohex-1-ene
CAS Registry NumberNot Available
SMILES
[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C
InChI Identifier
InChI=1S/C20H28/c1-7-16(2)10-8-11-17(3)13-14-19-18(4)12-9-15-20(19,5)6/h7-8,10-14H,1,9,15H2,2-6H3/b11-8+,16-10+,17-13+,19-14-
InChI KeyFWNRILWHNGFAIN-OYUWDNMLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cyclofarsesane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0022 g/lALOGPS
LogP6.81ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(6.81) g/LALOGPS
logP10(5.67) g/LChemAxon
logS10(-5.1) g/LALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity96.19 m³·mol⁻¹ChemAxon
Polarizability34.88 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.71231661259
DarkChem[M-H]-169.37331661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
anhydroretinol[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C2714.6Standard polar33892256
anhydroretinol[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C2091.0Standard non polar33892256
anhydroretinol[H]/C(=C(/[H])\C(\C)=C(/[H])\C(\[H])=C1\C(C)=CCCC1(C)C)/C(/[H])=C(\C)C=C2025.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - anhydroretinol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-1290000000-016a94e4ec3a2dd2b25e2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - anhydroretinol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - anhydroretinol 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 - anhydroretinol 10V, Positive-QTOFsplash10-014i-2490000000-ceaf9937108ecbc219e92017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 20V, Positive-QTOFsplash10-0fui-6950000000-7c7c89a4d9feac59ae372017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 40V, Positive-QTOFsplash10-0udi-9330000000-0f553bc1b3f267fd8fe42017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 10V, Negative-QTOFsplash10-014i-0090000000-9f98354a74dce8944e362017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 20V, Negative-QTOFsplash10-014i-0090000000-9499b10eec769375f21d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 40V, Negative-QTOFsplash10-0gbi-3980000000-39b950dafd407ad8e8da2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 10V, Negative-QTOFsplash10-014i-0490000000-192dc77c2569dcb54a8b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 20V, Negative-QTOFsplash10-014s-0950000000-42254474be47a902838c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 40V, Negative-QTOFsplash10-066r-4920000000-0f01aa95711ffe9127fe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 10V, Positive-QTOFsplash10-01b9-6960000000-08df1cff099abca5c75b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 20V, Positive-QTOFsplash10-009l-9730000000-f597d278a45f1426e7122021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - anhydroretinol 40V, Positive-QTOFsplash10-0fa9-9800000000-3d04abe1abfd3c3531f82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDDB02914
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5287678
PDB IDANR
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE5014
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.