Chaerophyllin (6CI); (3E,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methylene]dihydro-2(3H)-furanone

Details

• Internal ID: d06487af-88b4-4958-bbd4-37d21b9ecdcf
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: 4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methylidene]oxolan-2-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C=C2C(COC2=O)CC3=CC4=C(C=C3)OCO4)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C=C2C(COC2=O)CC3=CC4=C(C=C3)OCO4)OC
• InChI: InChI=1S/C21H20O6/c1-23-17-5-3-14(9-19(17)24-2)8-16-15(11-25-21(16)22)7-13-4-6-18-20(10-13)27-12-26-18/h3-6,8-10,15H,7,11-12H2,1-2H3
• InChI Key: CSKOHFAJPKLSBP-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₆
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.12598835 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.23
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• PD163094
• B0005-190039

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9930	99.30%
Caco-2	+	0.7273	72.73%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7603	76.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9332	93.32%
OATP1B3 inhibitior	+	0.9630	96.30%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9656	96.56%
P-glycoprotein inhibitior	+	0.8479	84.79%
P-glycoprotein substrate	-	0.7162	71.62%
CYP3A4 substrate	+	0.5784	57.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7972	79.72%
CYP3A4 inhibition	+	0.9591	95.91%
CYP2C9 inhibition	+	0.9399	93.99%
CYP2C19 inhibition	+	0.9801	98.01%
CYP2D6 inhibition	+	0.8096	80.96%
CYP1A2 inhibition	+	0.6598	65.98%
CYP2C8 inhibition	+	0.4521	45.21%
CYP inhibitory promiscuity	+	0.9845	98.45%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4437	44.37%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9005	90.05%
Skin irritation	-	0.7722	77.22%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8112	81.12%
Micronuclear	+	0.6874	68.74%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	+	0.5463	54.63%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.5894	58.94%
Acute Oral Toxicity (c)	III	0.6175	61.75%
Estrogen receptor binding	+	0.9069	90.69%
Androgen receptor binding	+	0.6592	65.92%
Thyroid receptor binding	+	0.6468	64.68%
Glucocorticoid receptor binding	+	0.7358	73.58%
Aromatase binding	-	0.5330	53.30%
PPAR gamma	+	0.7080	70.80%
Honey bee toxicity	-	0.7846	78.46%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9897	98.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.55%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.74%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.33%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.90%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.78%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.51%	91.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.34%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.67%	96.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.04%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.93%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.69%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.23%	95.89%
CHEMBL2535	P11166	Glucose transporter	87.54%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.48%	89.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.55%	95.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.17%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.10%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.46%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.69%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.77%	94.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.76%	93.00%

Plants that contains it

• Bupleurum salicifolium
• Bupleurum scorzonerifolium
• Jatropha gossypiifolia
• Montrouziera sphaeroidea

Cross-Links

• PubChem: 78384666
• LOTUS: LTS0064556
• wikiData: Q104969406