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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-22 21:17:08 UTC
Update Date2021-09-22 21:17:08 UTC
HMDB IDHMDB0301809
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-Arctiin
Description(-)-arctiin is a member of the class of compounds known as lignan glycosides. Lignan glycosides are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones (-)-arctiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-arctiin can be found in burdock, which makes (-)-arctiin a potential biomarker for the consumption of this food product.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H34O11
Average Molecular Weight534.5523
Monoisotopic Molecular Weight534.21011193
IUPAC Name(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one
Traditional Namearctiin
CAS Registry Number20362-31-6
SMILES
COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(OC)=C2)C=C1OC
InChI Identifier
InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1
InChI KeyXOJVHLIYNSOZOO-SWOBOCGESA-N
Chemical Taxonomy
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
  • 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 Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.71ALOGPS
logP1.17ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area153.37 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity132.26 m³·mol⁻¹ChemAxon
Polarizability54.3 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+226.31332859911
AllCCS[M+H-H2O]+224.59732859911
AllCCS[M+Na]+228.31832859911
AllCCS[M+NH4]+227.87532859911
AllCCS[M-H]-220.83632859911
AllCCS[M+Na-2H]-222.98532859911
AllCCS[M+HCOO]-225.49232859911
DeepCCS[M+H]+212.47630932474
DeepCCS[M-H]-210.65230932474
DeepCCS[M-2H]-243.93130932474
DeepCCS[M+Na]+218.08230932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 10V, Positive-QTOFsplash10-0609-0219060000-22c2a112cd172a49963c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 20V, Positive-QTOFsplash10-05i0-0329000000-8e8aa0ddc6f2c45aebf02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 40V, Positive-QTOFsplash10-0hii-0903000000-bb8563b6575aa033b0f52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 10V, Negative-QTOFsplash10-0089-1305190000-3798be4f0c41102e15982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 20V, Negative-QTOFsplash10-05fr-0109120000-1a5082c90489213e83812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 40V, Negative-QTOFsplash10-0abc-2019000000-5a59383d74a2143b2ee72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 10V, Positive-QTOFsplash10-007a-0828090000-f803cd592bea9e1a7bf62021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 20V, Positive-QTOFsplash10-000i-0914120000-813b99d319f0905ef6152021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 40V, Positive-QTOFsplash10-0080-2819310000-e564f38b7a37e3ff44022021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 10V, Negative-QTOFsplash10-001i-0003090000-3878468b16540d3190822021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 20V, Negative-QTOFsplash10-0ac0-2309670000-2dffd5d6218366f9cfb92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctiin 40V, Negative-QTOFsplash10-0a4i-6529210000-a290a4b53648a7e2705f2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB001444
KNApSAcK IDC00000646
Chemspider ID90827
KEGG Compound IDC16915
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1667101
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available