Record Information
Version1.0
Creation date2010-04-08 22:04:58 UTC
Update date2020-02-24 19:10:23 UTC
Primary IDFDB001442
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(-)-Arctigenin
Description(-)-Arctigenin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety (-)-Arctigenin is found, on average, in the highest concentration within burdocks (Arctium lappa) and sesames (Sesamum orientale) (-)-Arctigenin has also been detected, but not quantified in, cardoons (Cynara cardunculus) and grape wine. This could make (-)-arctigenin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-Arctigenin.
CAS Number7770-78-7
Structure
Thumb
Synonyms
SynonymSource
4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanoneHMDB
4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanoneHMDB
ArctigeninHMDB
(-)-ArctigeninKEGG
2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R-trans)-manual
2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-manual
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.2ALOGPS
logP3.44ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity100.12 m³·mol⁻¹ChemAxon
Polarizability38.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H24O6
IUPAC name(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
InChI IdentifierInChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
InChI KeyNQWVSMVXKMHKTF-JKSUJKDBSA-N
Isomeric SMILESCOC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC
Average Molecular Weight372.4117
Monoisotopic Molecular Weight372.1572885
Classification
Description Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • Methoxyphenol
  • Dimethoxybenzene
  • O-dimethoxybenzene
  • Phenoxy compound
  • Methoxybenzene
  • Anisole
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(-)-Arctigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udr-0902000000-a82290112ad63ba03dccSpectrum
Predicted GC-MS(-)-Arctigenin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kor-3973800000-2347d0d35e64e75b2b49Spectrum
Predicted GC-MS(-)-Arctigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(-)-Arctigenin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1900000000-94ffe376e556a84e04e2Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-2c7a991f2027b0e8dc39Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-0928000000-178d921541b9d4503c6fSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0900000000-42290b1e66720d9e2353Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-72b4027a78652bdd8eb9Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1900000000-7fb96b95e48e656b0645Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0916000000-47e3d42e55329b017ba7Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0900000000-1642e59faff2457a7cffSpectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0916000000-fb82e62c5852184489ecSpectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1900000000-ff811c876ea83a69a357Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1900000000-6b50e0e0840d80baa1cbSpectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1900000000-a9fd3c90bbf09fb0df59Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0926000000-2ab58c4998975ed5e47bSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-0850a6604476178cdab0Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0910000000-96f24efffea4aac77e10Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0926000000-a8895984ec2ac4ab9465Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0910000000-9c2761b3ac042651bd73Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1900000000-0684d0cb19a0e2a2bb34Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0910000000-784cae6debd6285bdcbeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0219000000-584468bac14267e31318Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bi-0849000000-e5165efc859c5b26acaaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h09-1900000000-c6366c49014c7cfa69a6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-1101ebe8048661a906d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05dr-0219000000-6a116c084f4196a8e9adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0269000000-a57a1d2446d72c2c7c98Spectrum
NMRNot Available
ChemSpider ID58506
ChEMBL IDNot Available
KEGG Compound IDC10545
Pubchem Compound ID64981
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID600
DrugBank IDNot Available
HMDB IDHMDB30087
CRC / DFC (Dictionary of Food Compounds) IDJPW07-G:LMW22-I
EAFUS IDNot Available
Dr. Duke IDARCTIGENIN|(-)-ARCTIGENIN
BIGG IDNot Available
KNApSAcK IDC00000609
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArctigenin
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 HIV22587 A substance that destroys or inhibits replication of viruses.DUKE
anti integrase23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti lymphomicDUKE
anti proliferantDUKE
anti TNF35222 A substance that diminishes the rate of a chemical reaction.DUKE
anti topoisomerase-II50750 A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
differentiatorDUKE
HIV-reverse-transcriptase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
immunomodulator50846 Biologically active substance whose activity affects or plays a role in the functioning of the immune system.DUKE
immunostimulant50847 A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
popoisomerase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.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.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.