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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:40 UTC
Update Date2022-03-07 02:52:25 UTC
HMDB IDHMDB0030087
Secondary Accession Numbers
  • HMDB30087
Metabolite Identification
Common 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.
Structure
Data?1563861935
Synonyms
ValueSource
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
Chemical FormulaC21H24O6
Average Molecular Weight372.4117
Monoisotopic Molecular Weight372.1572885
IUPAC Name(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Name(-)-arctigenin
CAS Registry Number7770-78-7
SMILES
COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point567.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility23.08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.470 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+190.54731661259
DarkChem[M-H]-187.64731661259
DeepCCS[M+H]+182.76830932474
DeepCCS[M-H]-180.4130932474
DeepCCS[M-2H]-213.89530932474
DeepCCS[M+Na]+189.11330932474
AllCCS[M+H]+190.832859911
AllCCS[M+H-H2O]+187.732859911
AllCCS[M+NH4]+193.632859911
AllCCS[M+Na]+194.432859911
AllCCS[M-H]-193.532859911
AllCCS[M+Na-2H]-193.832859911
AllCCS[M+HCOO]-194.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-ArctigeninCOC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC4925.3Standard polar33892256
(-)-ArctigeninCOC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC3131.4Standard non polar33892256
(-)-ArctigeninCOC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O)C(OC)=C2)C=C1OC3132.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Arctigenin,1TMS,isomer #1COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C)C(OC)=C2)C=C1OC3191.0Semi standard non polar33892256
(-)-Arctigenin,1TBDMS,isomer #1COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C2)C=C1OC3433.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Arctigenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-0902000000-a82290112ad63ba03dcc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Arctigenin GC-MS (1 TMS) - 70eV, Positivesplash10-0kor-3973800000-2347d0d35e64e75b2b492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Arctigenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Arctigenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-1900000000-94ffe376e556a84e04e22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 20V, Positive-QTOFsplash10-000i-0911000000-2c7a991f2027b0e8dc392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOFsplash10-052r-0928000000-178d921541b9d4503c6f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-0900000000-42290b1e66720d9e23532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 30V, Positive-QTOFsplash10-000i-0900000000-72b4027a78652bdd8eb92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 50V, Positive-QTOFsplash10-000i-1900000000-7fb96b95e48e656b06452021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-0916000000-47e3d42e55329b017ba72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-0900000000-1642e59faff2457a7cff2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOFsplash10-000i-0916000000-fb82e62c5852184489ec2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 50V, Positive-QTOFsplash10-000i-1900000000-ff811c876ea83a69a3572021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-1900000000-6b50e0e0840d80baa1cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-1900000000-a9fd3c90bbf09fb0df592021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOFsplash10-000i-0926000000-2ab58c4998975ed5e47b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 30V, Positive-QTOFsplash10-000i-0900000000-0850a6604476178cdab02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 40V, Positive-QTOFsplash10-000i-0910000000-96f24efffea4aac77e102021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-0926000000-a8895984ec2ac4ab94652021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 30V, Positive-QTOFsplash10-000i-0910000000-9c2761b3ac042651bd732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 50V, Positive-QTOFsplash10-000i-1900000000-0684d0cb19a0e2a2bb342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (-)-Arctigenin 6V, Positive-QTOFsplash10-000i-0910000000-784cae6debd6285bdcbe2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctigenin 10V, Positive-QTOFsplash10-00di-0219000000-584468bac14267e313182016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctigenin 20V, Positive-QTOFsplash10-00bi-0849000000-e5165efc859c5b26acaa2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctigenin 40V, Positive-QTOFsplash10-0h09-1900000000-c6366c49014c7cfa69a62016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctigenin 10V, Negative-QTOFsplash10-00di-0009000000-1101ebe8048661a906d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctigenin 20V, Negative-QTOFsplash10-05dr-0219000000-6a116c084f4196a8e9ad2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Arctigenin 40V, Negative-QTOFsplash10-00or-0269000000-a57a1d2446d72c2c7c982016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 ID600
FooDB IDFDB001442
KNApSAcK IDC00000609
Chemspider ID58506
KEGG Compound IDC10545
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArctigenin
METLIN IDNot Available
PubChem Compound64981
PDB IDNot Available
ChEBI ID391051
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1486671
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.. .