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Showing Compound (-)-Arctigenin (FDB001442)

Record Information
Version1.0
Creation date2010-04-08 22:04:58 UTC
Update date2025-11-18 22:31:16 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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
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-1900000000-94ffe376e556a84e04e22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-000i-0911000000-2c7a991f2027b0e8dc392021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-052r-0928000000-178d921541b9d4503c6f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0900000000-42290b1e66720d9e23532021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-72b4027a78652bdd8eb92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1900000000-7fb96b95e48e656b06452021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0916000000-47e3d42e55329b017ba72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0900000000-1642e59faff2457a7cff2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0916000000-fb82e62c5852184489ec2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1900000000-ff811c876ea83a69a3572021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1900000000-6b50e0e0840d80baa1cb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-1900000000-a9fd3c90bbf09fb0df592021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0926000000-2ab58c4998975ed5e47b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0900000000-0850a6604476178cdab02021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-0910000000-96f24efffea4aac77e102021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0926000000-a8895984ec2ac4ab94652021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-0910000000-9c2761b3ac042651bd732021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-000i-1900000000-0684d0cb19a0e2a2bb342021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-000i-0910000000-784cae6debd6285bdcbe2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0219000000-584468bac14267e313182016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00bi-0849000000-e5165efc859c5b26acaa2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0h09-1900000000-c6366c49014c7cfa69a62016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-1101ebe8048661a906d12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05dr-0219000000-6a116c084f4196a8e9ad2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-0269000000-a57a1d2446d72c2c7c982016-08-03View Spectrum
NMRNot Available
ChemSpider ID58506
ChEMBL IDCHEMBL435734
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 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti-integrase23924 An agent that blocks the activity of integrase, an enzyme essential for HIV replication, reducing viral integration into host DNA. Therapeutically, it's used to treat HIV infection, preventing the virus from replicating and slowing disease progression, commonly used in combination with other antiretroviral therapies.DUKE
Anti leukemic35610 An agent that targets and inhibits the growth of leukemia cells, playing a crucial role in cancer treatment. Therapeutically, it is used to induce remission, manage symptoms, and improve survival rates in patients with leukemia. Key medical uses include treating acute and chronic leukemia, lymphoma, and other hematological malignancies.DUKE
Anti-lymphomicAn agent that targets and destroys lymphatic cells that form tumors, playing a crucial role in cancer treatment. Therapeutically, it is used to manage lymphomas, with key medical applications in chemotherapy and immunotherapy to combat blood cell cancers.DUKE
Anti proliferantAn agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.DUKE
Anti TNF35222 An agent that blocks tumor necrosis factor, a pro-inflammatory cytokine, reducing inflammation and immune responses. Therapeutically used to treat autoimmune diseases, such as rheumatoid arthritis, psoriasis, and Crohn's disease, by mitigating inflammation and tissue damage.DUKE
Anti topoisomerase-II50750 An agent that inhibits topoisomerase-II, an enzyme involved in DNA replication. Therapeutically, it's used in cancer treatment, particularly in leukemia and lymphoma, to prevent DNA replication and induce cell death. Key medical uses include chemotherapy for various cancers, exploiting its ability to disrupt DNA processes and halt tumor growth.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
DifferentiatorAn agent that induces cell differentiation, promoting mature cell formation. Its biological role involves regulating cell growth and development. Therapeutically, it has applications in cancer treatment, helping to mature cancer cells, making them more susceptible to chemotherapy. Key medical uses include leukemia and other malignancies, where differentiation therapy can improve treatment outcomes.DUKE
HIV-reverse-transcriptase inhibitor23924 An agent that blocks the activity of reverse transcriptase, an enzyme essential for HIV replication, reducing viral load and slowing disease progression. Therapeutically, it is used to treat HIV/AIDS, often in combination with other antiretroviral medications to prevent drug resistance and manage symptoms.DUKE
Immunomodulator50846 An agent that regulates the immune system, modifying its response to maintain balance. Therapeutically, it's used to treat autoimmune diseases, prevent transplant rejection, and manage chronic inflammatory conditions, such as rheumatoid arthritis and multiple sclerosis.DUKE
Immunostimulant50847 An agent that stimulates the immune system, enhancing its response to infections and diseases. Therapeutically, it boosts the body's natural defenses, commonly used to treat immunodeficiency disorders, prevent infections, and support cancer treatment, as well as manage chronic conditions like hepatitis and HIV.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Phosphodiesterase inhibitor23924 An agent that blocks phosphodiesterase enzymes, increasing cyclic nucleotide levels, and enhancing cellular signaling. Therapeutically, it treats respiratory, cardiovascular, and neurological disorders, with key medical uses including managing erectile dysfunction, pulmonary hypertension, and chronic obstructive pulmonary disease (COPD).DUKE
Topoisomerase inhibitor23924 An agent that blocks the activity of topoisomerase enzymes, which unwind DNA during replication. Therapeutically, it prevents cancer cell growth, commonly used in managing various types of cancer, including leukemia, lymphoma, and solid tumors.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.