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Showing Compound (-)-Arctiin (FDB001444)

Record Information
Version1.0
Creation date2010-04-08 22:04:58 UTC
Update date2019-11-26 02:56:28 UTC
Primary IDFDB001444
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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.
CAS Number20362-31-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
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
Chemical FormulaC27H34O11
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
InChI IdentifierInChI=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
Isomeric SMILESCOC1=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
Average Molecular Weight534.5523
Monoisotopic Molecular Weight534.21011193
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
  • 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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0609-0219060000-22c2a112cd172a49963c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-0329000000-8e8aa0ddc6f2c45aebf02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hii-0903000000-bb8563b6575aa033b0f52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-1305190000-3798be4f0c41102e15982016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0109120000-1a5082c90489213e83812016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-2019000000-5a59383d74a2143b2ee72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007a-0828090000-f803cd592bea9e1a7bf62021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0914120000-813b99d319f0905ef6152021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-2819310000-e564f38b7a37e3ff44022021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0003090000-3878468b16540d3190822021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ac0-2309670000-2dffd5d6218366f9cfb92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6529210000-a290a4b53648a7e2705f2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJPW07-G:JRB08-U
EAFUS IDNot Available
Dr. Duke IDARCTIIN|ARCTIGENIN-4-BETA-D-GLUCOPYRANOSIDE|ARCTIGENIN-4-O-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00000646
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.