(3E,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methylidene]oxolan-2-one

Details

• Internal ID: a522bb3e-f97e-487a-9ce2-f06a4d1f7004
• Taxonomy: Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans
• IUPAC Name: (3E,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methylidene]oxolan-2-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)OC)C=C2C(COC2=O)CC3=CC4=C(C=C3)OCO4
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)OC)/C=C/2\[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4
• InChI: InChI=1S/C22H22O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,7-10,15H,6,11-12H2,1-3H3/b16-7+/t15-/m0/s1
• InChI Key: CJLVKDPRUXBTJQ-PLWLOYALSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₇
• Molecular Weight: 398.40 g/mol
• Exact Mass: 398.13655304 g/mol
• Topological Polar Surface Area (TPSA): 72.50 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.24
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

• (3E,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methylidene]oxolan-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9920	99.20%
Caco-2	+	0.7281	72.81%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7008	70.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9421	94.21%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.9724	97.24%
P-glycoprotein inhibitior	+	0.8371	83.71%
P-glycoprotein substrate	-	0.7925	79.25%
CYP3A4 substrate	+	0.5754	57.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7972	79.72%
CYP3A4 inhibition	+	0.9262	92.62%
CYP2C9 inhibition	+	0.8499	84.99%
CYP2C19 inhibition	+	0.9709	97.09%
CYP2D6 inhibition	+	0.5126	51.26%
CYP1A2 inhibition	-	0.5145	51.45%
CYP2C8 inhibition	+	0.4910	49.10%
CYP inhibitory promiscuity	+	0.9728	97.28%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4404	44.04%
Eye corrosion	-	0.9824	98.24%
Eye irritation	-	0.8862	88.62%
Skin irritation	-	0.7969	79.69%
Skin corrosion	-	0.9664	96.64%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7514	75.14%
Micronuclear	+	0.7074	70.74%
Hepatotoxicity	+	0.7875	78.75%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5802	58.02%
Acute Oral Toxicity (c)	III	0.5230	52.30%
Estrogen receptor binding	+	0.9175	91.75%
Androgen receptor binding	+	0.5537	55.37%
Thyroid receptor binding	+	0.6734	67.34%
Glucocorticoid receptor binding	+	0.8196	81.96%
Aromatase binding	-	0.5493	54.93%
PPAR gamma	+	0.7785	77.85%
Honey bee toxicity	-	0.7482	74.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9885	98.85%

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	96.62%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.38%	91.11%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.73%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.29%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.16%	92.62%
CHEMBL2581	P07339	Cathepsin D	94.26%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.92%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.38%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.38%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.94%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.63%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.61%	89.00%
CHEMBL2535	P11166	Glucose transporter	85.87%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.78%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.72%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.59%	85.14%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.29%	97.14%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.27%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.98%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.42%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	82.23%	94.73%

Plants that contains it

• Aglaia meridionalis
• Allium ursinum
• Ammi majus
• Anthriscus sylvestris
• Arcangelisia gusanlung
• Artemisia schmidtiana
• Brickellia pendula
• Bupleurum scorzonerifolium
• Citrus deliciosa
• Cladanthus scariosus
• Cleidion brevipetiolatum
• Copaifera paupera
• Crotalaria spectabilis
• Endosamara racemosa
• Entandrophragma cylindricum
• Escallonia virgata
• Ficus maxima
• Gleichenia polypodioides
• Hesperocyparis nevadensis
• Jacobaea erratica
• Juniperus thurifera
• Lathyrus linifolius
• Leptospermum scoparium
• Magnolia acuminata
• Neoboutonia mannii
• Onoclea struthiopteris
• Ophioglossum vulgatum
• Plectranthus amboinicus
• Plumbago europaea
• Reissantia indica
• Rhodanthe stricta
• Simmondsia chinensis
• Tabebuia rosea
• Tanacetum santolina
• Timonius kaniensis

Cross-Links

• PubChem: 11165431
• NPASS: NPC21430
• LOTUS: LTS0160944
• wikiData: Q104961359