Justicidin A

Details

• Internal ID: 2fde1efb-809b-4772-b23f-f39e775b17ba
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3C(=C2OC)COC3=O)C4=CC5=C(C=C4)OCO5)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3C(=C2OC)COC3=O)C4=CC5=C(C=C4)OCO5)OC
• InChI: InChI=1S/C22H18O7/c1-24-16-7-12-13(8-17(16)25-2)21(26-3)14-9-27-22(23)20(14)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3
• InChI Key: ANFSXHKDCKWWDB-UHFFFAOYSA-N
• Popularity: 73 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₇
• Molecular Weight: 394.40 g/mol
• Exact Mass: 394.10525291 g/mol
• Topological Polar Surface Area (TPSA): 72.40 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.93
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 25001-57-4
• Justicidins
• Justicidin-A
• UNII-Q58EXN1G4M
• Q58EXN1G4M
• CHEBI:6093
• 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
• 9-(benzo[d][1,3]dioxol-5-yl)-4,6,7-trimethoxynaphtho[2,3-c]furan-1(3H)-one
• diphyllin methyl ether
• 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-3H-benzo[f]isobenzofuran-1-one
• Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-
• JUSTICIDIN A [MI]
• SureCN168356
• SCHEMBL168356
• CHEMBL508532
• DTXSID40179709
• ANFSXHKDCKWWDB-UHFFFAOYSA-N
• AKOS040752209
• HY-117078
• CS-0063664
• E88985
• Q16897539
• 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxynaphtho[2,3-c]furan-1-(3H)-one
• NAPHTHO(2,3-C)FURAN-1(3H)-ONE, 4,6,7-TRIMETHOXY-9-(3,4-(METHYLENEDIOXY)PHENYL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	+	0.9045	90.45%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6974	69.74%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9493	94.93%
OATP1B3 inhibitior	+	0.9651	96.51%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9064	90.64%
P-glycoprotein inhibitior	+	0.7688	76.88%
P-glycoprotein substrate	-	0.8844	88.44%
CYP3A4 substrate	+	0.5553	55.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8360	83.60%
CYP3A4 inhibition	+	0.8826	88.26%
CYP2C9 inhibition	+	0.9061	90.61%
CYP2C19 inhibition	+	0.9355	93.55%
CYP2D6 inhibition	-	0.7937	79.37%
CYP1A2 inhibition	-	0.6855	68.55%
CYP2C8 inhibition	+	0.4900	49.00%
CYP inhibitory promiscuity	+	0.9414	94.14%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.3969	39.69%
Eye corrosion	-	0.9851	98.51%
Eye irritation	-	0.6537	65.37%
Skin irritation	-	0.8278	82.78%
Skin corrosion	-	0.9689	96.89%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7633	76.33%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.6964	69.64%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5534	55.34%
Acute Oral Toxicity (c)	III	0.4888	48.88%
Estrogen receptor binding	+	0.8903	89.03%
Androgen receptor binding	+	0.6946	69.46%
Thyroid receptor binding	+	0.7143	71.43%
Glucocorticoid receptor binding	+	0.9321	93.21%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6931	69.31%
Honey bee toxicity	-	0.7947	79.47%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9693	96.93%

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	97.38%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.99%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.41%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.56%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.46%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.91%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.55%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.55%	92.62%
CHEMBL2535	P11166	Glucose transporter	91.33%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.82%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	90.01%	80.96%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.82%	85.14%
CHEMBL1907	P15144	Aminopeptidase N	89.58%	93.31%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.86%	94.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.63%	95.53%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	84.95%	98.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.57%	96.09%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	84.46%	85.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.44%	96.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.50%	82.67%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.14%	92.38%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	81.83%	94.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.44%	97.14%

Plants that contains it

• Aquilaria sinensis
• Boenninghausenia albiflora
• Euphorbia franckiana
• Garcinia subelliptica
• Geranium nepalense
• Grindelia ciliata
• Haplophyllum cappadocicum
• Haplophyllum tuberculatum
• Hertia intermedia
• Justicia patentiflora
• Justicia procumbens
• Kippistia suaedifolia
• Monechma ciliatum
• Pelargonium reniforme
• Phyllanthus oligospermus
• Polygala amarella
• Solanum torvum
• Swertia angustifolia

Cross-Links

• PubChem: 159982
• NPASS: NPC239113
• ChEMBL: CHEMBL508532
• LOTUS: LTS0152201
• wikiData: Q16897539