(-)-Arctigenin (CED0006054)

Record Information

Version

1.0

Creation Date

2016-05-25 21:15:33 UTC

Update Date

2026-08-21 19:06:13 UTC

Accession Number

CHEM023730

Identification

Common Name

(-)-Arctigenin

Class

Small Molecule

Description

(-)-Arctigenin is an organic compound with the formula C21H24O6 and an average molecular weight of 372.41 g/mol. (-)-Arctigenin belongs to the tetrahydrofuran lignans, a subclass of furanoid lignans within the organic compounds. In industrial applications, the compound is used as an antioxidant. It has been recorded as being found in the preparation of vinegar, categorized under food, food processing & cookware.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

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

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	Yes	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	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0udr-0902000000-a82290112ad63ba03dcc	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0kor-3973800000-2347d0d35e64e75b2b49	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-94ffe376e556a84e04e2	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0911000000-2c7a991f2027b0e8dc39	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-052r-0928000000-178d921541b9d4503c6f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0900000000-42290b1e66720d9e2353	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0900000000-72b4027a78652bdd8eb9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-7fb96b95e48e656b0645	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0916000000-47e3d42e55329b017ba7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0900000000-1642e59faff2457a7cff	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0916000000-fb82e62c5852184489ec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-ff811c876ea83a69a357	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-6b50e0e0840d80baa1cb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-a9fd3c90bbf09fb0df59	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0926000000-2ab58c4998975ed5e47b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0900000000-0850a6604476178cdab0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0910000000-96f24efffea4aac77e10	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0926000000-a8895984ec2ac4ab9465	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0910000000-9c2761b3ac042651bd73	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-1900000000-0684d0cb19a0e2a2bb34	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-0910000000-784cae6debd6285bdcbe	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0219000000-584468bac14267e31318	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00bi-0849000000-e5165efc859c5b26acaa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0h09-1900000000-c6366c49014c7cfa69a6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-1101ebe8048661a906d1	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-05dr-0219000000-6a116c084f4196a8e9ad	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00or-0269000000-a57a1d2446d72c2c7c98	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0219000000-f01d38fefff61fbf31ac	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-1903000000-834e8b38e2b0e53b761f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0pi9-1947000000-bad24e81d8e9b45b9163	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-0009000000-11a2e76e9f81a2691d0b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0c00-0119000000-76fe23b69ee1976f9a19	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0005-4982000000-454e1e8cdb283a5cb026	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
8469.0	Log mg/kg	[4800:15000]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cytochrome P450 3A4	P08684	Humans	Predicted (SEA)	309.918
Click to view 3D structure	Aromatase	P11511	Humans	Predicted (SEA)	28.1036
Click to view 3D structure	Polyunsaturated fatty acid 5-lipoxygenase	P09917	Humans	Predicted (SEA)	43.4399
Click to view 3D structure	Sodium-dependent serotonin transporter	P31645	Humans	Predicted (SEA)	183.491
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	408.942
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	77.0707
Click to view 3D structure	Cytochrome P450 1A2	P05177	Humans	Predicted (SEA)	258.615
Click to view 3D structure	Sodium-dependent noradrenaline transporter	P23975	Humans	Predicted (SEA)	145.812
Click to view 3D structure	Carbonic anhydrase 2	Q3I4V7	Cryptococcus neoformans	Predicted (SEA)	26.2352
Click to view 3D structure	Carbonic anhydrase	Q5AJ71	Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)	Predicted (SEA)	29.5827
Click to view 3D structure	PROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)	P96878	Mycobacterium tuberculosis	Predicted (SEA)	27.4808
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	254.645
Click to view 3D structure	Histamine H2 receptor	P25021	Humans	Predicted (SEA)	90.2272
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	145.111
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	161.459
Click to view 3D structure	Cytochrome P450 2C8	P10632	Humans	Predicted (SEA)	86.724
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	219.146
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	187.694
Click to view 3D structure	Regulatory protein E2	P03118	Human papillomavirus type 1a	Predicted (SEA)	0.622794
Click to view 3D structure	Alpha-2C adrenergic receptor	P18825	Humans	Predicted (SEA)	161.304
Click to view 3D structure	Carbonic anhydrase 7	P43166	Humans	Predicted (SEA)	115.995
Click to view 3D structure	Cytochrome P450 2B6	P20813	Humans	Predicted (SEA)	26.858
Click to view 3D structure	Muscarinic acetylcholine receptor M4	P08173	Humans	Predicted (SEA)	107.743
Click to view 3D structure	Carbonic anhydrase 14	Q9ULX7	Humans	Predicted (SEA)	90.9279
Click to view 3D structure	Tissue factor	P13726	Humans	Predicted (SEA)	26.4687