Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2020-02-24 19:10:31 UTC
Primary IDFDB002438
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTracheloside
DescriptionTracheloside belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. Tracheloside has been detected, but not quantified in, a few different foods, such as fats and oils, herbs and spices, and safflowers (Carthamus tinctorius). This could make tracheloside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Tracheloside.
CAS Number33464-71-0
Structure
Thumb
Synonyms
SynonymSource
(-)-TrachelosideHMDB
Trachelosidedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.38 g/LALOGPS
logP1.02ALOGPS
logP0.31ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.79ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area173.6 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity133.72 m³·mol⁻¹ChemAxon
Polarizability56.07 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H34O12
IUPAC name4-[(3,4-dimethoxyphenyl)methyl]-3-hydroxy-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one
InChI IdentifierInChI=1S/C27H34O12/c1-34-17-6-4-14(9-19(17)35-2)8-16-13-37-26(32)27(16,33)11-15-5-7-18(20(10-15)36-3)38-25-24(31)23(30)22(29)21(12-28)39-25/h4-7,9-10,16,21-25,28-31,33H,8,11-13H2,1-3H3
InChI KeyLWYAMIUSVGPFKS-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C=C(CC2COC(=O)C2(O)CC2=CC(OC)=C(OC3OC(CO)C(O)C(O)C3O)C=C2)C=C1
Average Molecular Weight550.5517
Monoisotopic Molecular Weight550.205026552
Classification
Description Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassLignan glycosides
Sub ClassNot Available
Direct ParentLignan glycosides
Alternative Parents
Substituents
  • Lignan glycoside
  • Dibenzylbutyrolactone
  • Lignan lactone
  • Tetrahydrofuran lignan
  • 9,9p-epoxylignan
  • Furanoid lignan
  • Phenolic glycoside
  • Fatty acyl glycoside of mono- or disaccharide
  • Fatty acyl glycoside
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • Anisole
  • Alkyl aryl ether
  • Fatty acyl
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Acetal
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.90%; H 6.22%; O 34.87%DFC
Melting PointMp 168-170°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -60 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTracheloside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05as-6942260000-2426d86287749bdee4d3Spectrum
Predicted GC-MSTracheloside, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fmi-3922006000-2d8203309c5ec08df867Spectrum
Predicted GC-MSTracheloside, "Tracheloside,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTracheloside, TMS_3_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fe0-0329070000-229302209e65124822b12016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0439000000-d5cc767f04ebfe852c8a2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0913000000-3967bc3beda4dfc8beb12016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f72-1285090000-564d6ad59e10c35475412016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1339030000-e3502794bac3fac483052016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-2209000000-57a68803022cd006acc22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0101190000-02f9e74f6bd7203761432021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-1649180000-8231476d2085a730cdbf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059i-7639230000-ee0bee4b02884535bddd2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0104090000-a66abf583ba48d15974e2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0955270000-f2f733da92b2b6f752c02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-1923520000-839e75363de898826eec2021-09-22View Spectrum
NMRNot Available
ChemSpider ID26503677
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53462879
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30557
CRC / DFC (Dictionary of Food Compounds) IDMBB20-R:CLT74-I
EAFUS IDNot Available
Dr. Duke IDTRACHELOSIDE
BIGG IDNot Available
KNApSAcK IDC00032370
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti estrogenic35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti hypertensive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cardiosedative38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
cardiotonic38070 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.DUKE
respira inhibitor35222 A substance that diminishes the rate of a chemical reaction.DUKE
respirastimulantDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).