4-(1,3-Benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

Details

• Internal ID: fcb13f47-5b6a-4849-9dcd-501400fa80a6
• 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)methyl]oxolan-2-one
• SMILES (Canonical): COC1=C(C=C(C=C1)CC2C(COC2=O)CC3=CC4=C(C=C3)OCO4)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)CC2C(COC2=O)CC3=CC4=C(C=C3)OCO4)OC
• InChI: InChI=1S/C21H22O6/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/h3-6,9-10,15-16H,7-8,11-12H2,1-2H3
• InChI Key: IYBDDRJHJMFFBB-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.40 g/mol
• Exact Mass: 370.14163842 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• ACon1_001485
• NCGC00180457-01
• BRD-A01840690-001-01-8
• NCGC00180457-02!4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9894	98.94%
Caco-2	+	0.6951	69.51%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8048	80.48%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9259	92.59%
OATP1B3 inhibitior	+	0.9619	96.19%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9507	95.07%
P-glycoprotein inhibitior	+	0.7913	79.13%
P-glycoprotein substrate	-	0.7508	75.08%
CYP3A4 substrate	+	0.5455	54.55%
CYP2C9 substrate	+	0.5905	59.05%
CYP2D6 substrate	-	0.7552	75.52%
CYP3A4 inhibition	+	0.9593	95.93%
CYP2C9 inhibition	+	0.9142	91.42%
CYP2C19 inhibition	+	0.9757	97.57%
CYP2D6 inhibition	+	0.7186	71.86%
CYP1A2 inhibition	+	0.7348	73.48%
CYP2C8 inhibition	-	0.7133	71.33%
CYP inhibitory promiscuity	+	0.9441	94.41%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.4756	47.56%
Eye corrosion	-	0.9796	97.96%
Eye irritation	-	0.8897	88.97%
Skin irritation	-	0.8259	82.59%
Skin corrosion	-	0.9668	96.68%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8639	86.39%
Micronuclear	+	0.5759	57.59%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.5593	55.93%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.5099	50.99%
Acute Oral Toxicity (c)	III	0.6344	63.44%
Estrogen receptor binding	+	0.8917	89.17%
Androgen receptor binding	+	0.7639	76.39%
Thyroid receptor binding	+	0.5977	59.77%
Glucocorticoid receptor binding	+	0.6762	67.62%
Aromatase binding	-	0.6312	63.12%
PPAR gamma	+	0.5881	58.81%
Honey bee toxicity	-	0.7785	77.85%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9912	99.12%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.24%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.31%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.23%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.29%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.98%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.69%	92.62%
CHEMBL261	P00915	Carbonic anhydrase I	93.27%	96.76%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.09%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	92.87%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.93%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.04%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.91%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.74%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.53%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.21%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.44%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.29%	97.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.27%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.85%	99.17%
CHEMBL2535	P11166	Glucose transporter	82.67%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	81.63%	90.20%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.05%	97.50%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.43%	82.67%

Plants that contains it

• Bupleurum salicifolium
• Bursera schlechtendalii
• Bursera simaruba
• Hernandia nymphaeifolia
• Juniperus chinensis
• Phyllanthus urinaria
• Zanthoxylum beecheyanum

Cross-Links

• PubChem: 13916162
• LOTUS: LTS0006428
• wikiData: Q105122640