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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:59:52 UTC
Update Date2023-02-21 17:26:02 UTC
HMDB IDHMDB0037742
Secondary Accession Numbers
  • HMDB37742
Metabolite Identification
Common Namexi-5-Dodecanolide
Descriptionxi-5-Dodecanolide belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. Thus, XI-5-dodecanolide is considered to be a fatty ester. xi-5-Dodecanolide is a sweet, buttery, and coconut tasting compound. xi-5-Dodecanolide is found, on average, in the highest concentration within peppermints (Mentha X piperita). xi-5-Dodecanolide has also been detected, but not quantified in, a few different foods, such as blackberries (Rubus), coconuts (Cocos nucifera), and evergreen blackberries (Rubus laciniatus). This could make XI-5-dodecanolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on xi-5-Dodecanolide.
Structure
Data?1677000362
Synonyms
ValueSource
(+/-)-5-dodecanolideHMDB
(+/-)-6-heptyltetrahydro-2H-pyran-2-oneHMDB
(+/-)-delta-heptyl-delta-valerolactoneHMDB
5-DodecalactoneHMDB
5-Hydroxydodecanoic acid delta-lactoneHMDB
5-Hydroxydodecanoic acid lactoneHMDB
6-heptyltetrahydro-2H-Pyran-2-oneHMDB
delta-DodecalactoneHMDB
delta-DodecanolactoneHMDB
delta-Heptyl-delta-valerolactoneHMDB
Dodecan-5-olideHMDB
Dodecanoic acid, 5-hydroxy-, delta-lactoneHMDB
Dodecanolide-1,5HMDB
N-Heptyl-delta-valerolactoneHMDB
Δ-dodecalactoneGenerator
Chemical FormulaC12H22O2
Average Molecular Weight198.3019
Monoisotopic Molecular Weight198.161979948
IUPAC Name6-heptyloxan-2-one
Traditional Namedelta-dodecalactone
CAS Registry Number3051-22-7
SMILES
CCCCCCCC1CCCC(=O)O1
InChI Identifier
InChI=1S/C12H22O2/c1-2-3-4-5-6-8-11-9-7-10-12(13)14-11/h11H,2-10H2,1H3
InChI KeyQRPLZGZHJABGRS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassDelta valerolactones
Direct ParentDelta valerolactones
Alternative Parents
Substituents
  • Delta_valerolactone
  • Delta valerolactone
  • Oxane
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-12 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.019 g/LALOGPS
logP4.34ALOGPS
logP3.76ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.86 m³·mol⁻¹ChemAxon
Polarizability24.59 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
DarkChem[M+H]+148.16631661259
DarkChem[M-H]-145.83531661259
DeepCCS[M+H]+153.19830932474
DeepCCS[M-H]-149.39530932474
DeepCCS[M-2H]-187.05830932474
DeepCCS[M+Na]+162.35730932474
AllCCS[M+H]+150.332859911
AllCCS[M+H-H2O]+146.332859911
AllCCS[M+NH4]+154.032859911
AllCCS[M+Na]+155.132859911
AllCCS[M-H]-154.032859911
AllCCS[M+Na-2H]-154.932859911
AllCCS[M+HCOO]-156.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
xi-5-DodecanolideCCCCCCCC1CCCC(=O)O12435.3Standard polar33892256
xi-5-DodecanolideCCCCCCCC1CCCC(=O)O11603.8Standard non polar33892256
xi-5-DodecanolideCCCCCCCC1CCCC(=O)O11739.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - xi-5-Dodecanolide EI-B (Non-derivatized)splash10-006y-9000000000-6dde1f4e9eb6e77e29092017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - xi-5-Dodecanolide EI-B (Non-derivatized)splash10-006y-9000000000-6dde1f4e9eb6e77e29092018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-5-Dodecanolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-00gv-9300000000-81e2985e9c436226c5772016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-5-Dodecanolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-5-Dodecanolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - xi-5-Dodecanolide LC-ESI-QTOF , positive-QTOFsplash10-03e9-0900000000-4a1c0c068526fdf84a512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - xi-5-Dodecanolide LC-ESI-QTOF , positive-QTOFsplash10-03ka-3900000000-85aa811e6aabe9eb2fab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - xi-5-Dodecanolide 10V, Positive-QTOFsplash10-03e9-0900000000-edf9460e6f07bc10701b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - xi-5-Dodecanolide 10V, Positive-QTOFsplash10-03e9-0900000000-4a1c0c068526fdf84a512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - xi-5-Dodecanolide 20V, Positive-QTOFsplash10-03ka-3900000000-85aa811e6aabe9eb2fab2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 10V, Positive-QTOFsplash10-0002-0900000000-5faedf2b3da12ffb907d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 20V, Positive-QTOFsplash10-08fr-3900000000-30ec084bc09f83f3e01a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 40V, Positive-QTOFsplash10-052f-9200000000-19972997d12efa7d2d2f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 10V, Negative-QTOFsplash10-0f6t-0900000000-19f313ff46494d79b1ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 20V, Negative-QTOFsplash10-0f6t-3900000000-dc38a126e161e45a8bb02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 40V, Negative-QTOFsplash10-0006-9100000000-7265f487c6f2a25944112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 10V, Positive-QTOFsplash10-0a4j-9300000000-09c5d1f0cecc8213d1892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 20V, Positive-QTOFsplash10-052f-9100000000-136b583c75cfd1b47a702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 40V, Positive-QTOFsplash10-052f-9100000000-abfe093fcccf0157ec262021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 10V, Negative-QTOFsplash10-0002-0900000000-e1c4c7edfac216993e062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 20V, Negative-QTOFsplash10-0002-3900000000-ad70e93c53aebe76e52a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-5-Dodecanolide 40V, Negative-QTOFsplash10-0a6u-6900000000-eba8dee2f97ccb9a51ba2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB016873
KNApSAcK IDNot Available
Chemspider ID12314
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12844
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .