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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:50:55 UTC
Update Date2022-03-07 02:54:16 UTC
HMDB IDHMDB0034920
Secondary Accession Numbers
  • HMDB34920
Metabolite Identification
Common NameTaraxerol
DescriptionTaraxerol, also known as alnulin, is a naturally-occurring pentacyclic oleanane-type triterpenoid. It can be found in plants such as Taraxacum officinale (Asteraceae; dandelion), Alnus glutinosa (Betulaceae), Litsea dealbata (Lauraceae), Skimmia spp. (Rutaceae), Dorstenia spp. (Moraceae), Maytenus spp. (Celastraceae), and Alchornea latifolia (Euphobiaceae). Taraxerol is an oleanan-3-ol with an alpha-methyl substituent at position 13, a missing methyl group at position 14, and a double bond between 14 and 15. A large number of medicinal plants are known to have this compound in their leaves, roots or seed oil (PMID: 26009688 ). Taraxerol has shown the anti-inflammatory effects in vitro, it can disrupt the activation of the enzymes MAP3K7 (TAK1), protein kinase B (PKB or Akt), and NF-κB. By doing so, it may inhibit the expression of proinflammatory mediators in microphages (PMID: 23333629). Taraxerol also exhibits anti-carcinogenic activity. In vivo two-stage carcinogenesis tests of mouse skin tumor showed that taraxerol can inhibit the induction of Epstein-Barr virus early antigen (EBV-EA) by the tumor initiator 7,12-dimethylbenz(a)anthracene (DMBA) and the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) (PMID: 10408235 ) (Wikipedia ). Taraxerol is found in alcoholic beverages.
Structure
Data?1563862635
Synonyms
ValueSource
(3beta)-D-Friedoolean-14-en-3-olHMDB
AlnulinHMDB
D-Friedoolean-14-en-3beta-olHMDB
Skimmiol?HMDB
3beta-TaraxerolMeSH
D-Friedoolean-14-en-3 beta-olMeSH
Chemical FormulaC30H50O
Average Molecular Weight426.7174
Monoisotopic Molecular Weight426.386166222
IUPAC Name4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4,4a,5,6,6a,8,8a,9,10,11,12,12a,12b,13,14,14a,14b-icosahydropicen-3-ol
Traditional Nametaraxerol
CAS Registry Number127-22-0
SMILES
CC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C1
InChI Identifier
InChI=1S/C30H50O/c1-25(2)17-18-27(5)13-9-21-29(7)14-10-20-26(3,4)24(31)12-16-28(20,6)22(29)11-15-30(21,8)23(27)19-25/h9,20,22-24,31H,10-19H2,1-8H3
InChI KeyGGGUGZHBAOMSFJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as scalarane sesterterpenoids. These are sesterterpenoids with a structure based on the scalarane backbone. Scalarane is a tetracyclic compound, which is similar the homoandrostane with five methyl groups at the 4-, 4-, 8-, 17-, 17a-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesterterpenoids
Direct ParentScalarane sesterterpenoids
Alternative Parents
Substituents
  • Scalarane sesterterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point282 - 283 °CNot Available
Boiling Point409.00 to 410.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP3.195 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility6.9e-05 g/LALOGPS
logP7.2ALOGPS
logP7.4ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)19.49ChemAxon
pKa (Strongest Basic)-0.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity131.91 m³·mol⁻¹ChemAxon
Polarizability54.39 ųChemAxon
Number of Rings5ChemAxon
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]+199.46131661259
DarkChem[M-H]-194.18731661259
DeepCCS[M+H]+213.29430932474
DeepCCS[M-H]-210.93630932474
DeepCCS[M-2H]-244.88830932474
DeepCCS[M+Na]+220.11630932474
AllCCS[M+H]+217.832859911
AllCCS[M+H-H2O]+216.032859911
AllCCS[M+NH4]+219.432859911
AllCCS[M+Na]+219.932859911
AllCCS[M-H]-213.332859911
AllCCS[M+Na-2H]-215.032859911
AllCCS[M+HCOO]-217.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TaraxerolCC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C12663.6Standard polar33892256
TaraxerolCC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C13392.6Standard non polar33892256
TaraxerolCC1(C)CCC2(C)CC=C3C4(C)CCC5C(C)(C)C(O)CCC5(C)C4CCC3(C)C2C13393.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Taraxerol,1TMS,isomer #1CC1(C)CCC2(C)CC=C3C(C)(CCC4C3(C)CCC3C(C)(C)C(O[Si](C)(C)C)CCC43C)C2C13354.9Semi standard non polar33892256
Taraxerol,1TBDMS,isomer #1CC1(C)CCC2(C)CC=C3C(C)(CCC4C3(C)CCC3C(C)(C)C(O[Si](C)(C)C(C)(C)C)CCC43C)C2C13597.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Taraxerol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-0219500000-793fa49b829c7c9709642017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Taraxerol GC-MS (1 TMS) - 70eV, Positivesplash10-001i-1011900000-186d7d36edca5fd916222017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Taraxerol 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 - Taraxerol 10V, Positive-QTOFsplash10-0a6r-0001900000-55a012724749e9910efc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 20V, Positive-QTOFsplash10-0a6r-1668900000-a815b8aa5a8e77b3948e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 40V, Positive-QTOFsplash10-0hh0-1569100000-12304aa318eaca43c7bd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 10V, Negative-QTOFsplash10-004i-0000900000-a5f272b047d0bed70dd52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 20V, Negative-QTOFsplash10-004i-0000900000-b12658710e0349eca4fb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 40V, Negative-QTOFsplash10-052f-1019500000-0c45941ca686fb4d77cf2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 10V, Positive-QTOFsplash10-004i-0002900000-17e13fb85ee36d97d4682021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 20V, Positive-QTOFsplash10-0a4i-2219300000-a65a5f1cae40e7e77a372021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 40V, Positive-QTOFsplash10-000f-2920000000-392cc5c23c3270d14a282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 10V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 20V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Taraxerol 40V, Negative-QTOFsplash10-004i-0000900000-590c9e4adfdd12b64d932021-09-25Wishart 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 IDFDB013505
KNApSAcK IDC00003758
Chemspider ID305433
KEGG Compound IDC08637
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTaraxerol
METLIN IDNot Available
PubChem Compound344467
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1594101
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. Sharma K, Zafar R: Occurrence of taraxerol and taraxasterol in medicinal plants. Pharmacogn Rev. 2015 Jan-Jun;9(17):19-23. doi: 10.4103/0973-7847.156317. [PubMed:26009688 ]
  6. Takasaki M, Konoshima T, Tokuda H, Masuda K, Arai Y, Shiojima K, Ageta H: Anti-carcinogenic activity of Taraxacum plant. II. Biol Pharm Bull. 1999 Jun;22(6):606-10. doi: 10.1248/bpb.22.606. [PubMed:10408235 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.