4-(1,3-Benzodioxol-5-ylmethyl)-3-[(3,4-dihydroxy-5-methoxyphenyl)methyl]-3-hydroxyoxolan-2-one

Details

• Internal ID: f349866a-f241-4d93-8da2-ad7b4da8ad36
• 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-dihydroxy-5-methoxyphenyl)methyl]-3-hydroxyoxolan-2-one
• SMILES (Canonical): COC1=CC(=CC(=C1O)O)CC2(C(COC2=O)CC3=CC4=C(C=C3)OCO4)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O)O)CC2(C(COC2=O)CC3=CC4=C(C=C3)OCO4)O
• InChI: InChI=1S/C20H20O8/c1-25-17-7-12(5-14(21)18(17)22)8-20(24)13(9-26-19(20)23)4-11-2-3-15-16(6-11)28-10-27-15/h2-3,5-7,13,21-22,24H,4,8-10H2,1H3
• InChI Key: GENGJDIMWQYHFT-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.40 g/mol
• Exact Mass: 388.11581759 g/mol
• Topological Polar Surface Area (TPSA): 115.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 1.52
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9304	93.04%
Caco-2	-	0.6936	69.36%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7816	78.16%
OATP2B1 inhibitior	-	0.7172	71.72%
OATP1B1 inhibitior	+	0.9103	91.03%
OATP1B3 inhibitior	+	0.9581	95.81%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6886	68.86%
P-glycoprotein inhibitior	-	0.5686	56.86%
P-glycoprotein substrate	-	0.7006	70.06%
CYP3A4 substrate	+	0.6222	62.22%
CYP2C9 substrate	-	0.6039	60.39%
CYP2D6 substrate	-	0.7714	77.14%
CYP3A4 inhibition	+	0.5778	57.78%
CYP2C9 inhibition	-	0.7863	78.63%
CYP2C19 inhibition	-	0.5230	52.30%
CYP2D6 inhibition	-	0.8356	83.56%
CYP1A2 inhibition	-	0.8292	82.92%
CYP2C8 inhibition	+	0.5123	51.23%
CYP inhibitory promiscuity	-	0.8133	81.33%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4405	44.05%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.8015	80.15%
Skin irritation	-	0.8018	80.18%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5109	51.09%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	+	0.6302	63.02%
skin sensitisation	-	0.8123	81.23%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.6238	62.38%
Acute Oral Toxicity (c)	III	0.5908	59.08%
Estrogen receptor binding	+	0.9035	90.35%
Androgen receptor binding	+	0.5839	58.39%
Thyroid receptor binding	+	0.6213	62.13%
Glucocorticoid receptor binding	+	0.6458	64.58%
Aromatase binding	+	0.5805	58.05%
PPAR gamma	+	0.7029	70.29%
Honey bee toxicity	-	0.8359	83.59%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9600	96.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.58%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.67%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.97%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	97.10%	92.62%
CHEMBL2581	P07339	Cathepsin D	95.27%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.14%	96.09%
CHEMBL261	P00915	Carbonic anhydrase I	94.43%	96.76%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.40%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.34%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.21%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.28%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.15%	95.89%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	87.48%	94.80%
CHEMBL4208	P20618	Proteasome component C5	85.58%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.16%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.01%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.58%	89.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.15%	90.24%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.21%	93.40%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.72%	97.09%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.58%	97.50%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.53%	96.95%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.35%	80.78%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.19%	97.25%

Plants that contains it

• Taiwania cryptomerioides

Cross-Links

• PubChem: 163034517
• LOTUS: LTS0181617
• wikiData: Q105007241