Arctigenin

Details

• Internal ID: e3d600a7-5e26-468e-9970-d7e03d02a324
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• SMILES (Canonical): COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)O)OC)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O)OC)OC
• InChI: 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
• Popularity: 521 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.40 g/mol
• Exact Mass: 372.15728848 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 2.99
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 7

Synonyms

• (-)-Arctigenin
• 7770-78-7
• (+/-)-Arctigenin
• Arctigenin, (+/-)-
• UNII-U76MR9VS6M
• U76MR9VS6M
• Arctigenin, trans-((+/-)-
• C21H24O6
• (3R,4R)-4-(3,4-dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
• 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)-
• CHEBI:79
• ARCTIGENIN, (-)-
• UNII-2FD8L150E7
• 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-
• ARCTIGENIN, TRANS-(-)-
• 2FD8L150E7
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• (3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone
• 144901-91-7
• 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-rel-
• 2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, trans-
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3- [(4-hydroxy-3-methoxyphenyl)methyl]-2-tetrahydrofuranone
• Arctigenen
• 2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-
• Tocris-1777
• ARCTIGENIN [INCI]
• SCHEMBL381820
• CHEMBL435734
• MEGxp0_001799
• ACon1_000416
• DTXSID60998919
• HMS3268E18
• HMS3412H04
• HMS3676H04
• HY-N0035
• BDBM50375656
• HB0119
• MFCD00870597
• s3897
• STL565840
• AKOS015897121
• CCG-268327
• NCGC00025291-01
• NCGC00025291-02
• NCGC00025291-03
• NCGC00025291-04
• AC-33952
• AS-56162
• LS-69358
• (-)-Arctigenin, >=95% (LC/MS-ELSD)
• A865172
• SR-01000597504
• Q-100825
• Q4787603
• SR-01000597504-1
• BRD-K53523901-001-01-0
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-oxidanyl-phenyl)methyl]oxolan-2-one
• (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxy-phenyl)methyl]tetrahydrofuran-2-one
• (3R,4R)-4-[(3,4-DIMETHOXYPHENYL)METHYL]DIHYDRO-3-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-2(3H)-FURANONE;2(3H)-FURANONE,4-[(3,4-DIMETHOXYPHENYL)METHYL]DIHYDRO-3-[(4-HYDROXY-3-METHOXYPHENYL)METHYL]-,(3R,4R);(-)-ARCTIGENIN;ARCTIGENIN;ARCTIGENIN(P)
• (3R-trans)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy- 3-methoxyphenyl)methyl]-4,5-dihydrofuran-2(3H)-one
• 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-Furanone
• 4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-Furanone
• EQC

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9775	97.75%
Caco-2	+	0.6992	69.92%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.9082	90.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9355	93.55%
OATP1B3 inhibitior	+	0.8850	88.50%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8229	82.29%
P-glycoprotein inhibitior	+	0.6511	65.11%
P-glycoprotein substrate	-	0.7383	73.83%
CYP3A4 substrate	+	0.5156	51.56%
CYP2C9 substrate	-	0.5898	58.98%
CYP2D6 substrate	-	0.7380	73.80%
CYP3A4 inhibition	+	0.7960	79.60%
CYP2C9 inhibition	+	0.8948	89.48%
CYP2C19 inhibition	+	0.8994	89.94%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.8349	83.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8717	87.17%
Carcinogenicity (trinary)	Non-required	0.6148	61.48%
Eye corrosion	-	0.9859	98.59%
Eye irritation	-	0.8688	86.88%
Skin irritation	-	0.8704	87.04%
Skin corrosion	-	0.9862	98.62%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7674	76.74%
Micronuclear	-	0.5108	51.08%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.8689	86.89%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.6955	69.55%
Acute Oral Toxicity (c)	III	0.6374	63.74%
Estrogen receptor binding	+	0.8968	89.68%
Androgen receptor binding	+	0.7763	77.63%
Thyroid receptor binding	+	0.6150	61.50%
Glucocorticoid receptor binding	+	0.7223	72.23%
Aromatase binding	+	0.5889	58.89%
PPAR gamma	+	0.6667	66.67%
Honey bee toxicity	-	0.8748	87.48%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5849	58.49%
Fish aquatic toxicity	+	0.9911	99.11%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3356	P05177	Cytochrome P450 1A2	31622.78 nM	AC50	via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	2.5 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	15848.9 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3587	Q02750	Dual specificity mitogen-activated protein kinase kinase 1	1 nM	IC50	PMID: 18077363
CHEMBL4040	P28482	MAP kinase ERK2	12589.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.93%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.42%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.87%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.45%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.63%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.00%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.47%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.75%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.22%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.06%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.71%	94.00%
CHEMBL1255126	O15151	Protein Mdm4	84.45%	90.20%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.02%	85.14%
CHEMBL2535	P11166	Glucose transporter	83.75%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.00%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.07%	89.00%

Plants that contains it

• Acacia kempeana
• Achillea tuzsonii
• Aframomum sulcatum
• Alhagi pseudalhagi subsp. persarum
• Anthriscus sylvestris
• Arctium lappa
• Asplenium septentrionale
• Baillonella toxisperma
• Brachylaena ramiflora
• Bupleurum salicifolium
• Carthamus tinctorius
• Castanopsis cuspidata
• Centaurea arenaria
• Centaurea axillaris
• Centaurea calcitrapa
• Centaurea cineraria subsp. cineraria
• Centaurea deflexa
• Centaurea macrocephala
• Centaurea nigra
• Centaurea paui
• Centaurea phrygia
• Centaurea regia
• Centaurea scabiosa
• Centaurea scoparia
• Centaurea solstitialis
• Coespeletia moritziana
• Colliguaja salicifolia
• Cynara cardunculus
• Daphne feddei
• Daphne genkwa
• Decaisnea fargesii
• Dendrobium crepidatum
• Dendrobium thyrsiflorum
• Diospyros buxifolia
• Forsythia koreana
• Forsythia ovata
• Forsythia suspensa
• Forsythia viridissima
• Haplophyllum patavinum
• Hymenaea courbaril
• Ipomoea cairica
• Kielmeyera albopunctata
• Laburnum watereri
• Lessertia frutescens
• Montanoa guatemalensis
• Nuxia oppositifolia
• Oenanthe aquatica
• Onopordum acaulon
• Onopordum boissierianum
• Orbivestus leopoldii
• Plectocephalus americanus
• Polygonatum stenophyllum
• Psephellus schischkinii
• Pteris biaurita subsp. fornicata
• Saussurea candicans
• Saussurea gossipiphora
• Saussurea medusa
• Saussurea parviflora
• Saussurea salicifolia
• Senecio variabilis
• Taiwania cryptomerioides
• Teucrium lanigerum
• Torreya jackii
• Torreya nucifera
• Trachelospermum asiaticum
• Trachelospermum axillare
• Trachelospermum jasminoides
• Vitis vinifera

Cross-Links

• PubChem: 64981
• NPASS: NPC176814
• ChEMBL: CHEMBL435734
• LOTUS: LTS0194121
• wikiData: Q4787603