Record Information
Version1.0
Creation date2010-04-08 22:04:58 UTC
Update date2015-07-20 21:40:31 UTC
Primary IDFDB001444
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Arctiin
DescriptionNot Available
CAS Number20362-31-6
Structure
Thumb
Synonyms
SynonymSource
Arctigenin-4-glucosidebiospider
Arctiin (8CI)biospider
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP1.71ALOGPS
logP1.17ChemAxon
logS-3.5ALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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 KeyInChIKey=XOJVHLIYNSOZOO-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 Weight535
Monoisotopic Molecular Weight534
Classification
DescriptionThis compound 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
  • Furanoid lignan
  • 9,9p-epoxylignan
  • Tetrahydrofuran lignan
  • Lignan lactone
  • Fatty acyl glycoside
  • Phenolic glycoside
  • Alkyl glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • Oxane
  • Monosaccharide
  • Gamma butyrolactone
  • Saccharide
  • Monocyclic benzene moiety
  • Oxolane
  • Secondary alcohol
  • Polyol
  • Lactone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0609-0219060000-22c2a112cd172a49963cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05i0-0329000000-8e8aa0ddc6f2c45aebf0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hii-0903000000-bb8563b6575aa033b0f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0089-1305190000-3798be4f0c41102e1598View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0109120000-1a5082c90489213e8381View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0abc-2019000000-5a59383d74a2143b2ee7View in MoNA
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
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 cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
narcotic35482 A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.DUKE
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.