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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:52:51 UTC
Update Date2023-02-21 17:26:38 UTC
HMDB IDHMDB0038557
Secondary Accession Numbers
  • HMDB38557
Metabolite Identification
Common Namexi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran
Descriptionxi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran, also known as 4-methyl-2-(2-methyl-1-propen-1-yl)-3,6-dihydro-2H-pyran or neryl oxide, belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran is a celery, cortex, and diphenyl oxide tasting compound. xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran has been detected, but not quantified in, a few different foods, such as black elderberries (Sambucus nigra), gingers (Zingiber officinale), and white wine. This could make XI-3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran a potential biomarker for the consumption of these foods. xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 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 xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran.
Structure
Data?1677000398
Synonyms
ValueSource
3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyranChEBI
3,6-Dihydro-4-methyl-2-(2-methylpropen-1-yl)-2H-pyranChEBI
3,6-Dihydro-4-methyl-2-(2-methylpropenyl)-2H-pyranChEBI
4-Methyl-2-(2-methyl-1-propen-1-yl)-3,6-dihydro-2H-pyranChEBI
4-Methyl-2-(2-methylprop-1-enyl)-3,6-dihydro-2H-pyranChEBI
Neryl oxideChEBI
Nerol oxideMeSH
Chemical FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name4-methyl-2-(2-methylprop-1-en-1-yl)-3,6-dihydro-2H-pyran
Traditional Name4-methyl-2-(2-methylprop-1-en-1-yl)-3,6-dihydro-2H-pyran
CAS Registry NumberNot Available
SMILES
CC(C)=CC1CC(C)=CCO1
InChI Identifier
InChI=1S/C10H16O/c1-8(2)6-10-7-9(3)4-5-11-10/h4,6,10H,5,7H2,1-3H3
InChI KeyFRISMOQHTLZZRP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassNot Available
Direct ParentPyrans
Alternative Parents
Substituents
  • Pyran
  • Oxacycle
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point201.00 to 202.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility77.23 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.984 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.4 g/LALOGPS
logP3.17ALOGPS
logP2.43ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.19 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.34831661259
DarkChem[M-H]-131.79131661259
DeepCCS[M+H]+134.8230932474
DeepCCS[M-H]-131.01130932474
DeepCCS[M-2H]-168.45530932474
DeepCCS[M+Na]+143.85330932474
AllCCS[M+H]+130.732859911
AllCCS[M+H-H2O]+126.132859911
AllCCS[M+NH4]+135.032859911
AllCCS[M+Na]+136.232859911
AllCCS[M-H]-135.132859911
AllCCS[M+Na-2H]-136.632859911
AllCCS[M+HCOO]-138.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyranCC(C)=CC1CC(C)=CCO11425.3Standard polar33892256
xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyranCC(C)=CC1CC(C)=CCO11103.8Standard non polar33892256
xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyranCC(C)=CC1CC(C)=CCO11130.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran EI-B (Non-derivatized)splash10-014i-9000000000-c7728956a05defa6ddc52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran EI-B (Non-derivatized)splash10-014i-9000000000-c7728956a05defa6ddc52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran GC-MS (Non-derivatized) - 70eV, Positivesplash10-0py0-9500000000-f3d29d3d5c62599d2c0a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 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 - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 10V, Positive-QTOFsplash10-0udi-1900000000-368a69826e2649ef98452015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 20V, Positive-QTOFsplash10-0uyj-9500000000-354b9b1ed1b49bee92012015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 40V, Positive-QTOFsplash10-0gb9-9000000000-0b3a09563832b518f44d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 10V, Negative-QTOFsplash10-0udi-1900000000-44e765cd2daec5bef6c72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 20V, Negative-QTOFsplash10-0udi-5900000000-8df464ef69bfcc97c6882015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 40V, Negative-QTOFsplash10-067i-9100000000-7599f12f73eed131a3e12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 10V, Positive-QTOFsplash10-0hft-9600000000-3fd3ea10d3d866324b8a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 20V, Positive-QTOFsplash10-0aor-9000000000-8b15d65ba863a573bcf22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 40V, Positive-QTOFsplash10-014l-9000000000-bcdd6d965b814b14515c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 20V, Negative-QTOFsplash10-0udi-2900000000-a60813a4e90968d64c3f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-3,6-Dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran 40V, Negative-QTOFsplash10-014i-9200000000-1741d255b40beefc00fe2021-09-25Wishart 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
  • 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 IDFDB020082
KNApSAcK IDC00056008
Chemspider ID55214
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61275
PDB IDNot Available
ChEBI ID144705
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1001891
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.. .