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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:36:00 UTC
Update Date2021-10-13 05:41:16 UTC
HMDB IDHMDB0013804
Secondary Accession Numbers
  • HMDB13804
Metabolite Identification
Common Namebeta-Damascenone
Descriptionbeta-Damascenone, also known as damascenone, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, beta-damascenone is considered to be an isoprenoid. beta-Damascenone exists in all eukaryotes, ranging from yeast to plants to humans. beta-Damascenone is a sweet, apple, and apple.rose tasting compound. beta-Damascenone is found, on average, in the highest concentration within red wine. beta-Damascenone has also been detected, but not quantified in, several different foods, such as german camomiles (Matricaria recutita), common grapes (Vitis vinifera), apples (Malus pumila), garden tomatoes (Solanum lycopersicum), and grapes (Vitis). This could make beta-damascenone a potential biomarker for the consumption of these foods. beta-Damascenone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on beta-Damascenone.
Structure
Data?1582753145
Synonyms
ValueSource
(2E)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneChEBI
(e)-1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneChEBI
(e)-beta-DamascenoneChEBI
beta-(e)-DamascenoneChEBI
DamascenoneChEBI
trans-beta-DamascenoneChEBI
trans-DamascenoneChEBI
(e)-b-DamascenoneGenerator
(e)-Β-damascenoneGenerator
b-(e)-DamascenoneGenerator
Β-(e)-damascenoneGenerator
trans-b-DamascenoneGenerator
trans-Β-damascenoneGenerator
b-DamascenoneGenerator
Β-damascenoneGenerator
1-(2,6,6-Trimethyl-1,3-cyclohexadien-1-yl)-2-buten-1-oneHMDB
Chemical FormulaC13H18O
Average Molecular Weight190.286
Monoisotopic Molecular Weight190.1357652
IUPAC Name(2E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
Traditional Namedamascenone
CAS Registry Number23696-85-7
SMILES
C\C=C\C(=O)C1=C(C)C=CCC1(C)C
InChI Identifier
InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+
InChI KeyPOIARNZEYGURDG-FNORWQNLSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnones
Alternative Parents
Substituents
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point274.00 to 276.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility12.48 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.042 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP10(4.02) g/LALOGPS
logP10(3.68) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.02 m³·mol⁻¹ChemAxon
Polarizability22.61 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]+153.58330932474
DeepCCS[M-H]-151.22530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-DamascenoneC\C=C\C(=O)C1=C(C)C=CCC1(C)C1800.4Standard polar33892256
beta-DamascenoneC\C=C\C(=O)C1=C(C)C=CCC1(C)C1388.6Standard non polar33892256
beta-DamascenoneC\C=C\C(=O)C1=C(C)C=CCC1(C)C1374.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Damascenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-01dm-5900000000-4bcd624fdf9c5e42b8872016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Damascenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Damascenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Damascenone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Damascenone 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 - beta-Damascenone 10V, Positive-QTOFsplash10-0006-1900000000-8da6e151fea92abe412a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 20V, Positive-QTOFsplash10-00kg-6900000000-2069d91b82e6511da0ae2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 40V, Positive-QTOFsplash10-014l-9200000000-6695f41d1b443f4da5982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 10V, Negative-QTOFsplash10-000i-0900000000-3f94da9b260ed91041b82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 20V, Negative-QTOFsplash10-000i-2900000000-7afc8b9366085d67da732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 40V, Negative-QTOFsplash10-007n-4900000000-d38de494cceadf7b6a172016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 10V, Negative-QTOFsplash10-000i-0900000000-797743ba698bddb677b12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 20V, Negative-QTOFsplash10-00di-0900000000-d9210597b39735810ebf2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 40V, Negative-QTOFsplash10-0ab9-2900000000-4ac82453126eb07d119f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 10V, Positive-QTOFsplash10-022c-0900000000-3c6a17c1864038197fc52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 20V, Positive-QTOFsplash10-05fr-2900000000-7fc87120284ef620e86a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Damascenone 40V, Positive-QTOFsplash10-0ac0-7900000000-3e0424c46a79abc4667d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015480
KNApSAcK IDC00035536
Chemspider ID4517997
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDamascenone
METLIN IDNot Available
PubChem Compound5366074
PDB IDNot Available
ChEBI ID67251
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1441071
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available