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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:36:30 UTC
Update Date2022-03-07 02:54:56 UTC
HMDB IDHMDB0036467
Secondary Accession Numbers
  • HMDB36467
Metabolite Identification
Common Namealpha-Humulene
Descriptionalpha-Humulene, also known as alpha-caryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, alpha-humulene is considered to be an isoprenoid lipid molecule. alpha-Humulene is found in allspice. alpha-Humulene is a constituent of many essential oils including hops (Humulus lupulus) and cloves (Syzygium aromaticum).
Structure
Data?1601246420
Synonyms
ValueSource
(1E,4E,8E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneChEBI
(e,e,e)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneChEBI
alpha-CaryophylleneChEBI
HumuleneChEBI
a-CaryophylleneGenerator
Α-caryophylleneGenerator
a-HumuleneGenerator
Α-humuleneGenerator
(1E,4E,8E)-a-HumuleneHMDB
(1E,4E,8E)-Α-humuleneHMDB
(±)-alpha-humuleneHMDB
(±)-α-humuleneHMDB
alpha-HumuleneChEBI
Chemical FormulaC15H24
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
IUPAC Name(1E,4E,8E)-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-HRGUGZIWSA-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
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point99.00 to 100.00 °C. @ 3.00 mm HgThe Good Scents Company Information System
Water Solubility0.014 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.592 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability21.08 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]+160.71230932474
DeepCCS[M-H]-158.35430932474
DeepCCS[M-2H]-191.30830932474
DeepCCS[M+Na]+166.80630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-HumuleneC\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC11747.4Standard polar33892256
alpha-HumuleneC\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC11464.1Standard non polar33892256
alpha-HumuleneC\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC11451.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Humulene GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0920000000-6a79f6794db42ee36f8b2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Humulene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - alpha-Humulene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9300000000-28c84729e712b8966f102015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 10V, Positive-QTOFsplash10-0a4i-0290000000-d1375940e9b7ed7922b42017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 20V, Positive-QTOFsplash10-0a4i-2930000000-cdb29a58477970796a702017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 40V, Positive-QTOFsplash10-00kr-4900000000-788e8bfc0021846819ae2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 10V, Negative-QTOFsplash10-0udi-0090000000-8ecbabe7146ad27627522017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 20V, Negative-QTOFsplash10-0udi-0390000000-984bd28446d79854bd712017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 40V, Negative-QTOFsplash10-01ri-1900000000-139cbaab33ea7f90de6c2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 40V, Negative-QTOFsplash10-0f79-0930000000-3fa88d27850dde91abb92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 10V, Positive-QTOFsplash10-0a4i-0090000000-c084f3d998cc56a199d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 20V, Positive-QTOFsplash10-0a4i-0090000000-c084f3d998cc56a199d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - alpha-Humulene 40V, Positive-QTOFsplash10-0079-0910000000-09f78ba2b16bf7aadb822021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
FooDB IDFDB097297
KNApSAcK IDC00003147
Chemspider ID4444853
KEGG Compound IDC09684
BioCyc IDCPD-8233
BiGG IDNot Available
Wikipedia LinkHumulene
METLIN IDNot Available
PubChem Compound5281520
PDB IDNot Available
ChEBI ID5768
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1027221
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.