ContaminantDB: (-)-Arctigenin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-25 21:15:33 UTC

Update Date

2016-11-09 01:17:46 UTC

Accession Number

CHEM023730

Identification

Common Name

(-)-Arctigenin

Class

Small Molecule

Description

(-)-Arctigenin is found in burdock. (-)-Arctigenin is isolated from Cnicus benedictus, Forsythia viridissima, Arctium lappa, Ipomoea cairica and others (CCD).Arctigenin is a lignan found in certain plants of the Asteraceae , including the Greater burdock (Arctium lappa) and Saussurea heteromalla. It has shown antiviral and anticancer effects. It is the aglycone of arctiin. (Wikipedia

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanone	HMDB
4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanone	HMDB
Arctigenin	HMDB
(-)-Arctigenin	KEGG

Chemical Formula

C₂₁H₂₄O₆

Average Molecular Mass

372.412 g/mol

Monoisotopic Mass

372.157 g/mol

CAS Registry Number

7770-78-7

IUPAC Name

(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

Traditional Name

(-)-arctigenin

SMILES

COC1=CC=C(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=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 Key

NQWVSMVXKMHKTF-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.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone 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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

lignan (CHEBI:79 )
Lignans (C10545 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.2	ALOGPS
logP	3.44	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.95	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	100.12 m³·mol⁻¹	ChemAxon
Polarizability	38.87 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udr-0902000000-a82290112ad63ba03dcc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0kor-3973800000-2347d0d35e64e75b2b49	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-1900000000-94ffe376e556a84e04e2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-2c7a991f2027b0e8dc39	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0928000000-178d921541b9d4503c6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0900000000-42290b1e66720d9e2353	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-72b4027a78652bdd8eb9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-1900000000-7fb96b95e48e656b0645	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0916000000-47e3d42e55329b017ba7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0900000000-1642e59faff2457a7cff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0916000000-fb82e62c5852184489ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-1900000000-ff811c876ea83a69a357	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-1900000000-6b50e0e0840d80baa1cb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-1900000000-a9fd3c90bbf09fb0df59	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0926000000-2ab58c4998975ed5e47b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0900000000-0850a6604476178cdab0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0910000000-96f24efffea4aac77e10	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0926000000-a8895984ec2ac4ab9465	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-000i-0910000000-9c2761b3ac042651bd73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-1900000000-0684d0cb19a0e2a2bb34	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-000i-0910000000-784cae6debd6285bdcbe	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0219000000-584468bac14267e31318	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00bi-0849000000-e5165efc859c5b26acaa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0h09-1900000000-c6366c49014c7cfa69a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-1101ebe8048661a906d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05dr-0219000000-6a116c084f4196a8e9ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-0269000000-a57a1d2446d72c2c7c98	Spectrum