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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:36:30 UTC
Update Date2018-05-20 00:29:23 UTC
HMDB IDHMDB0036467
Secondary Accession Numbers
  • HMDB36467
Metabolite Identification
Common Namealpha-Humulene
DescriptionAlpha-Humulene, also known as Α-humulene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Alpha-Humulene exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Alpha-Humulene has been primarily detected in feces. Within the cell, Alpha-humulene is primarily located in the membrane (predicted from logP) and cytoplasm. Alpha-Humulene is a woody tasting compound that can be found in a number of food items such as chinese cinnamon, hyssop, common sage, and cloves. This makes Alpha-humulene a potential biomarker for the consumption of these food products.
Structure
Thumb
Synonyms
ValueSource
(1E,4E,8E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneHMDB
(1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4,8-trieneHMDB
(1E,4E,8E)-alpha-HumuleneHMDB
(1E,4E,8E)-Humula-1(11),4,8-trieneHMDB
(e,e,e)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-(1E,4E,8E)-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-(e,e,e)-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-cycloundeca-1,4,8-trieneHMDB
3,7,10-HumulatrieneHMDB
a-Caryophyllene (obsol.)HMDB
a-HumuleneHMDB
alpha -HumulenHMDB
alpha -HumuleneHMDB
alpha -Humulene (alpha -caryophyllene)HMDB
alpha -HumulenenHMDB
alpha-CaryophylleneHMDB
HumuleneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name(1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene
Traditional Namehumulene
CAS Registry Number6753-98-6
SMILES
C\C1=C\CC(C)(C)\C=C/C\C(C)=C/CC1
InChI Identifier
InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6-,13-7-,14-10-
InChI KeyFAMPSKZZVDUYOS-KXWHQPPKSA-N
Chemical Taxonomy
DescriptionThis compound 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 olefin
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP6.07ALOGPS
logP4.88ChemAxon
logS-4.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.55 m³·mol⁻¹ChemAxon
Polarizability26.18 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0920000000-3e5845e9275b1b3231faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-d1375940e9b7ed7922b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2930000000-cdb29a58477970796a70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4900000000-788e8bfc0021846819aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-8ecbabe7146ad2762752View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-984bd28446d79854bd71View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ri-1900000000-139cbaab33ea7f90de6cView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not Quantified Adult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative Colitis
details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015360
KNApSAcK IDC00003147
Chemspider ID5006149
KEGG Compound IDC09684
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6508206
PDB IDNot Available
ChEBI ID5768
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chaves JS, Leal PC, Pianowisky L, Calixto JB: Pharmacokinetics and tissue distribution of the sesquiterpene alpha-humulene in mice. Planta Med. 2008 Nov;74(14):1678-83. doi: 10.1055/s-0028-1088307. Epub 2008 Oct 24. [PubMed:18951339 ]
  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.