Arctigenic acid

Details

• Internal ID: c0980a24-4da7-46d2-9788-ae1ea2ea366e
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: (2R,3R)-3-[(3,4-dimethoxyphenyl)methyl]-4-hydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]butanoic acid
• InChI: InChI=1S/C21H26O7/c1-26-18-7-5-13(11-20(18)28-3)8-15(12-22)16(21(24)25)9-14-4-6-17(23)19(10-14)27-2/h4-7,10-11,15-16,22-23H,8-9,12H2,1-3H3,(H,24,25)/t15-,16+/m0/s1
• InChI Key: WFRZWIDPAWVEAS-JKSUJKDBSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆O₇
• Molecular Weight: 390.40 g/mol
• Exact Mass: 390.16785316 g/mol
• Topological Polar Surface Area (TPSA): 105.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9437	94.37%
Caco-2	-	0.5316	53.16%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.9106	91.06%
OATP2B1 inhibitior	-	0.8572	85.72%
OATP1B1 inhibitior	+	0.9183	91.83%
OATP1B3 inhibitior	+	0.8593	85.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7510	75.10%
P-glycoprotein inhibitior	-	0.4457	44.57%
P-glycoprotein substrate	-	0.8100	81.00%
CYP3A4 substrate	-	0.5610	56.10%
CYP2C9 substrate	+	0.5905	59.05%
CYP2D6 substrate	-	0.7920	79.20%
CYP3A4 inhibition	+	0.5190	51.90%
CYP2C9 inhibition	+	0.5000	50.00%
CYP2C19 inhibition	-	0.5136	51.36%
CYP2D6 inhibition	-	0.8967	89.67%
CYP1A2 inhibition	+	0.6047	60.47%
CYP2C8 inhibition	+	0.5993	59.93%
CYP inhibitory promiscuity	-	0.5118	51.18%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.7660	76.60%
Carcinogenicity (trinary)	Non-required	0.7322	73.22%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8632	86.32%
Skin irritation	-	0.8461	84.61%
Skin corrosion	-	0.9817	98.17%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7558	75.58%
Micronuclear	-	0.6100	61.00%
Hepatotoxicity	-	0.7446	74.46%
skin sensitisation	-	0.9159	91.59%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6339	63.39%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8575	85.75%
Acute Oral Toxicity (c)	III	0.6907	69.07%
Estrogen receptor binding	+	0.8468	84.68%
Androgen receptor binding	+	0.7780	77.80%
Thyroid receptor binding	+	0.5537	55.37%
Glucocorticoid receptor binding	+	0.6460	64.60%
Aromatase binding	-	0.5148	51.48%
PPAR gamma	+	0.6336	63.36%
Honey bee toxicity	-	0.9055	90.55%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7604	76.04%
Fish aquatic toxicity	+	0.9847	98.47%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1255126	O15151	Protein Mdm4	97.98%	90.20%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.50%	99.17%
CHEMBL2581	P07339	Cathepsin D	95.08%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.70%	86.33%
CHEMBL2535	P11166	Glucose transporter	90.32%	98.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	88.90%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.87%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.71%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.11%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.55%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.30%	96.00%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	80.24%	97.88%

Plants that contains it

• Arctium lappa

Cross-Links

• PubChem: 102397297
• NPASS: NPC181045
• LOTUS: LTS0209606
• wikiData: Q105304138