Justicidin E

Details

• Internal ID: f7e9e86c-f6ee-4c5b-a0df-6de6322108a1
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 5-(1,3-benzodioxol-5-yl)-6H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• SMILES (Canonical): C1C2=C(C=C3C=C4C(=CC3=C2C5=CC6=C(C=C5)OCO6)OCO4)C(=O)O1
• SMILES (Isomeric): C1C2=C(C=C3C=C4C(=CC3=C2C5=CC6=C(C=C5)OCO6)OCO4)C(=O)O1
• InChI: InChI=1S/C20H12O6/c21-20-13-3-11-5-17-18(26-9-25-17)6-12(11)19(14(13)7-22-20)10-1-2-15-16(4-10)24-8-23-15/h1-6H,7-9H2
• InChI Key: VSMWRDYVLPCABE-UHFFFAOYSA-N
• Popularity: 78 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₂O₆
• Molecular Weight: 348.30 g/mol
• Exact Mass: 348.06338810 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 27792-97-8
• B41555M19R
• NSC-309692
• Furo(3',4':6,7)naphtho(2,3-d)-1,3-dioxol-6(8H)-one, 9-(1,3-benzodioxol-5-yl)-
• DTXSID40182117
• Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(8H)-one, 9-(1,3-benzodioxol-5-yl)-
• RefChem:924019
• DTXCID50104608
• Justicidin-E
• NSC309692
• UNII-B41555M19R
• NSC 309692
• CHEMBL304236
• justicidin
• JUSTICIDINE E
• SCHEMBL7659399
• SCHEMBL29582148
• SCHEMBL30637547
• CBA79297
• BDBM50280961
• 5-(1,3-benzodioxol-5-yl)-6H-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one
• Q27274333
• 5-(1,3-benzodioxol-5-yl)-6H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one
• 9-Benzo[1,3]dioxol-5-yl-8H-furo[3'',4'':6,7]naphtho[2,3-d][1,3]dioxol-6-one
• FURO(3',4':6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(8H)-ONE, 9-(3,4-(METHYLENEDIOXY)PHENYL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9957	99.57%
Caco-2	+	0.6837	68.37%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7512	75.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9538	95.38%
OATP1B3 inhibitior	+	0.9335	93.35%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8888	88.88%
P-glycoprotein inhibitior	-	0.4383	43.83%
P-glycoprotein substrate	-	0.9440	94.40%
CYP3A4 substrate	-	0.5103	51.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8614	86.14%
CYP3A4 inhibition	+	0.7711	77.11%
CYP2C9 inhibition	+	0.8494	84.94%
CYP2C19 inhibition	+	0.8099	80.99%
CYP2D6 inhibition	+	0.6366	63.66%
CYP1A2 inhibition	+	0.8281	82.81%
CYP2C8 inhibition	-	0.7108	71.08%
CYP inhibitory promiscuity	+	0.8494	84.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Warning	0.4785	47.85%
Eye corrosion	-	0.9753	97.53%
Eye irritation	+	0.7416	74.16%
Skin irritation	-	0.6039	60.39%
Skin corrosion	-	0.9489	94.89%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5250	52.50%
Micronuclear	+	0.7774	77.74%
Hepatotoxicity	+	0.6802	68.02%
skin sensitisation	-	0.6613	66.13%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.6699	66.99%
Acute Oral Toxicity (c)	III	0.7249	72.49%
Estrogen receptor binding	+	0.8364	83.64%
Androgen receptor binding	+	0.7871	78.71%
Thyroid receptor binding	+	0.6707	67.07%
Glucocorticoid receptor binding	+	0.8541	85.41%
Aromatase binding	+	0.6911	69.11%
PPAR gamma	+	0.7120	71.20%
Honey bee toxicity	-	0.8204	82.04%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9670	96.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	500 nM; 70 nM	IC50; IC50	DOI: 10.1016/S0960-894X(01)81016-7; DOI: 10.1016/S0960-894X(01)81016-7

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.80%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.29%	93.40%
CHEMBL1951	P21397	Monoamine oxidase A	95.86%	91.49%
CHEMBL2581	P07339	Cathepsin D	94.78%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.28%	94.80%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	92.15%	80.96%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.76%	91.11%
CHEMBL240	Q12809	HERG	90.95%	89.76%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.28%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.38%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.66%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.19%	94.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.11%	92.62%
CHEMBL2535	P11166	Glucose transporter	86.52%	98.75%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	84.86%	93.24%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.01%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	84.00%	93.31%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.95%	85.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.39%	96.12%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.25%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.75%	96.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.62%	99.23%
CHEMBL5543	Q9Y463	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	82.24%	94.70%
CHEMBL2039	P27338	Monoamine oxidase B	81.98%	92.51%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.84%	95.53%
CHEMBL3761	Q9HCG7	Beta-glucosidase	80.57%	99.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.45%	96.09%

Plants that contains it

• Hypoestes purpurea
• Justicia hyssopifolia
• Oenothera odorata
• Rostellularia procumbens
• Vitex peduncularis

Cross-Links

• PubChem: 363128
• NPASS: NPC24193
• ChEMBL: CHEMBL304236
• LOTUS: LTS0002789
• wikiData: Q27274333