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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:28:32 UTC
Update Date2021-10-13 07:11:26 UTC
HMDB IDHMDB0038195
Secondary Accession Numbers
  • HMDB38195
Metabolite Identification
Common NameXanthorrhizol
DescriptionXanthorrhizol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Xanthorrhizol.
Structure
Data?1563863155
Synonyms
ValueSource
(-)-5-(1,5-Dimethyl-4-hexenyl)-2-methylphenolHMDB
(R)-(-)-XanthorrhizolHMDB
(R)-5-(1,5-Dimethyl-4-hexenyl)-O-cresolHMDB
(R)-5-(1-5-Dimethyl-4-hexenyl)-2-methylphenolHMDB
5-(1,5-Dimethyl-4-hexenyl)-(-)-O-cresolHMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methyl-(-)-phenolHMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methylphenolHMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol, 9ciHMDB
5-[(1R)-1,5-Dimethyl-4-hexenyl]-2-methyl-phenolHMDB
Chemical FormulaC15H22O
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
IUPAC Name2-methyl-5-(6-methylhept-5-en-2-yl)phenol
Traditional Name2-methyl-5-(6-methylhept-5-en-2-yl)phenol
CAS Registry Number30199-26-9
SMILES
CC(CCC=C(C)C)C1=CC(O)=C(C)C=C1
InChI Identifier
InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3
InChI KeyFKWGCEDRLNNZOZ-UHFFFAOYSA-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
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • P-cymene
  • O-cresol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Toluene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point326.00 to 327.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.45 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.480The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP10(5.64) g/LALOGPS
logP10(5.09) g/LChemAxon
logS10(-3.9) g/LALOGPS
pKa (Strongest Acidic)10.42ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.07 m³·mol⁻¹ChemAxon
Polarizability27.06 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.9431661259
DarkChem[M-H]-151.67431661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
XanthorrhizolCC(CCC=C(C)C)C1=CC(O)=C(C)C=C12623.7Standard polar33892256
XanthorrhizolCC(CCC=C(C)C)C1=CC(O)=C(C)C=C11683.1Standard non polar33892256
XanthorrhizolCC(CCC=C(C)C)C1=CC(O)=C(C)C=C11747.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xanthorrhizol,1TMS,isomer #1CC(C)=CCCC(C)C1=CC=C(C)C(O[Si](C)(C)C)=C11757.7Semi standard non polar33892256
Xanthorrhizol,1TBDMS,isomer #1CC(C)=CCCC(C)C1=CC=C(C)C(O[Si](C)(C)C(C)(C)C)=C12003.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xanthorrhizol GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-5910000000-bbbc808402d4ed1b9d872017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthorrhizol GC-MS (1 TMS) - 70eV, Positivesplash10-05di-9380000000-5efc594d791232cfba9e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xanthorrhizol 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 - Xanthorrhizol 10V, Positive-QTOFsplash10-014i-1490000000-7b7917bbd2d076a6a1bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Positive-QTOFsplash10-014i-3930000000-f36e65d14851d985f07c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Positive-QTOFsplash10-0ldi-9500000000-5dae3bd921c5b051d0772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Negative-QTOFsplash10-014i-0090000000-e9ece6fa864d7f85bd6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Negative-QTOFsplash10-014i-0190000000-825f4354c46942faba2f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Negative-QTOFsplash10-0zgr-2920000000-ed263b9c3352ae00c36f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Negative-QTOFsplash10-014i-0690000000-832a55e37cc53c2790222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Negative-QTOFsplash10-001i-0900000000-9c4703d7c228cc18545c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Positive-QTOFsplash10-0a4i-9500000000-6361694e7914d5c8167b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Positive-QTOFsplash10-05ox-9200000000-ded2bd26eb1ced7c2c222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Positive-QTOFsplash10-052f-9600000000-92500c706afd0d6d2d872021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB017434
KNApSAcK IDC00011622
Chemspider ID453998
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound520468
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1516951
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Mustaffa F, Indurkar J, Ismail S, Shah M, Mansor SM: An antimicrobial compound isolated from Cinnamomum iners leaves with activity against methicillin-resistant Staphylococcus aureus. Molecules. 2011 Apr 8;16(4):3037-47. doi: 10.3390/molecules16043037. [PubMed:21478819 ]
  2. Handayani T, Sakinah S, Nallappan M, Pihie AH: Regulation of p53-, Bcl-2- and caspase-dependent signaling pathway in xanthorrhizol-induced apoptosis of HepG2 hepatoma cells. Anticancer Res. 2007 Mar-Apr;27(2):965-71. [PubMed:17465228 ]
  3. Lee LY, Shim JS, Rukayadi Y, Hwang JK: Antibacterial activity of xanthorrhizol isolated from Curcuma xanthorrhiza Roxb. against foodborne pathogens. J Food Prot. 2008 Sep;71(9):1926-30. [PubMed:18810881 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.