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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:49:56 UTC
Update Date2022-03-07 02:55:01 UTC
HMDB IDHMDB0036667
Secondary Accession Numbers
  • HMDB36667
Metabolite Identification
Common NameZerumbone
DescriptionZerumbone 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 Zerumbone.
Structure
Data?1563862906
Synonyms
ValueSource
(e,e,e)-2,6,9,9-Tetramethyl-2,6,10-cycloundecatrien-1-oneHMDB
2,6,9,9-Tetramethyl-2,6,10-cycloundecatrien-1-oneHMDB
2,6,9,9-Tetramethylcycloundeca-2,6,10-trien-1-oneHMDB
2,6,9-Humulatrien-8-oneHMDB
Chemical FormulaC15H22O
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
IUPAC Name(2Z,6Z,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
Traditional Name(2Z,6Z,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-trien-1-one
CAS Registry Number471-05-6
SMILES
C\C1=C\CC(C)(C)\C=C\C(=O)\C(C)=C/CC1
InChI Identifier
InChI=1S/C15H22O/c1-12-6-5-7-13(2)14(16)9-11-15(3,4)10-8-12/h7-9,11H,5-6,10H2,1-4H3/b11-9+,12-8-,13-7-
InChI KeyGIHNTRQPEMKFKO-RTTFEGKLSA-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
  • Humulane sesquiterpenoid
  • Sesquiterpenoid
  • Cyclic ketone
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point66 - 67 °CNot Available
Boiling Point321.00 to 322.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.168 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.04 g/LALOGPS
logP5.15ALOGPS
logP4.57ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity72.22 m³·mol⁻¹ChemAxon
Polarizability26.3 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
DeepCCS[M+H]+163.10430932474
DeepCCS[M-H]-160.74630932474
DeepCCS[M-2H]-193.63230932474
DeepCCS[M+Na]+169.19730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ZerumboneC\C1=C\CC(C)(C)\C=C\C(=O)\C(C)=C/CC12134.4Standard polar33892256
ZerumboneC\C1=C\CC(C)(C)\C=C\C(=O)\C(C)=C/CC11658.4Standard non polar33892256
ZerumboneC\C1=C\CC(C)(C)\C=C\C(=O)\C(C)=C/CC11699.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Zerumbone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0090000000-37543c5e9d48fdc4c4a72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Zerumbone 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 - Zerumbone 10V, Positive-QTOFsplash10-014i-0290000000-6bec49a6c089ce6f8a862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 20V, Positive-QTOFsplash10-014i-4960000000-c3df3c26a51bc308ae4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 40V, Positive-QTOFsplash10-0uxr-9510000000-9bd089c820b83951c37c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 10V, Negative-QTOFsplash10-014i-0090000000-4de13643894f1d738bdd2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 20V, Negative-QTOFsplash10-014i-0290000000-c1e809b09a77ef38d9502016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 40V, Negative-QTOFsplash10-0udi-3910000000-1935d57489b9deead68f2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 10V, Positive-QTOFsplash10-014i-0090000000-eda9112d52fe3b01c3ae2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 20V, Positive-QTOFsplash10-0udi-0090000000-cdd594c2311b8d6fa9c62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 40V, Positive-QTOFsplash10-000i-0920000000-00239ebc69223e922c1c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 10V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 20V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Zerumbone 40V, Negative-QTOFsplash10-0uxr-0490000000-fbf18a8ce07ee2cd12bb2021-09-22Wishart 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 IDFDB015595
KNApSAcK IDC00012467
Chemspider ID4522489
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5372142
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1065781
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kirana C, McIntosh GH, Record IR, Jones GP: Antitumor activity of extract of Zingiber aromaticum and its bioactive sesquiterpenoid zerumbone. Nutr Cancer. 2003;45(2):218-25. [PubMed:12881017 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.