Justicidin B

Details

• Internal ID: 08244723-10cb-489d-a8b1-7fa8c4141747
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1H-benzo[f][2]benzofuran-3-one
• SMILES (Canonical): COC1=CC2=CC3=C(C(=C2C=C1OC)C4=CC5=C(C=C4)OCO5)C(=O)OC3
• SMILES (Isomeric): COC1=CC2=CC3=C(C(=C2C=C1OC)C4=CC5=C(C=C4)OCO5)C(=O)OC3
• InChI: InChI=1S/C21H16O6/c1-23-16-7-12-5-13-9-25-21(22)20(13)19(14(12)8-17(16)24-2)11-3-4-15-18(6-11)27-10-26-15/h3-8H,9-10H2,1-2H3
• InChI Key: RTDRYYULUYRTAN-UHFFFAOYSA-N
• Popularity: 86 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆O₆
• Molecular Weight: 364.30 g/mol
• Exact Mass: 364.09468823 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.92
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

• 17951-19-8
• UNII-RQQ8T34V5F
• RQQ8T34V5F
• 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1H-benzo[f][2]benzofuran-3-one
• ST077116
• C10636
• Naphtho[2,3-c]furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-
• 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-1H-benzo[f]isobenzofuran-3-one
• Naphtho(2,3-c)furan-1(3H)-one, 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-
• AC1L9DKN
• JUSTICIDIN B [MI]
• SureCN4733970
• CHEBI:6094
• SCHEMBL4733970
• DTXSID70939232
• CPD-13455
• AKOS004110690
• HY-114275
• CS-0081082
• E88979
• Q27107062
• 9-(2H-1,3-Benzodioxol-5-yl)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one
• NAPHTHO(2,3-C)FURAN-1(3H)-ONE, 6,7-DIMETHOXY-9-(3,4-(METHYLENEDIOXY)PHENYL)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9927	99.27%
Caco-2	+	0.8779	87.79%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7625	76.25%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9425	94.25%
OATP1B3 inhibitior	+	0.9649	96.49%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8810	88.10%
P-glycoprotein inhibitior	+	0.7232	72.32%
P-glycoprotein substrate	-	0.8344	83.44%
CYP3A4 substrate	+	0.5377	53.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8360	83.60%
CYP3A4 inhibition	+	0.9348	93.48%
CYP2C9 inhibition	+	0.9716	97.16%
CYP2C19 inhibition	+	0.9766	97.66%
CYP2D6 inhibition	+	0.6561	65.61%
CYP1A2 inhibition	+	0.5380	53.80%
CYP2C8 inhibition	-	0.6021	60.21%
CYP inhibitory promiscuity	+	0.9546	95.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Warning	0.4177	41.77%
Eye corrosion	-	0.9817	98.17%
Eye irritation	-	0.5547	55.47%
Skin irritation	-	0.7884	78.84%
Skin corrosion	-	0.9637	96.37%
Ames mutagenesis	+	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3763	37.63%
Micronuclear	+	0.7674	76.74%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.6507	65.07%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.6267	62.67%
Acute Oral Toxicity (c)	III	0.7135	71.35%
Estrogen receptor binding	+	0.9044	90.44%
Androgen receptor binding	+	0.7890	78.90%
Thyroid receptor binding	+	0.7111	71.11%
Glucocorticoid receptor binding	+	0.9292	92.92%
Aromatase binding	+	0.5702	57.02%
PPAR gamma	+	0.6298	62.98%
Honey bee toxicity	-	0.8232	82.32%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9709	97.09%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.39%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.01%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.00%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.30%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.01%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.30%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.87%	95.56%
CHEMBL230	P35354	Cyclooxygenase-2	93.25%	89.63%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	93.25%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.14%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.99%	94.80%
CHEMBL240	Q12809	HERG	90.91%	89.76%
CHEMBL1951	P21397	Monoamine oxidase A	90.27%	91.49%
CHEMBL2535	P11166	Glucose transporter	88.00%	98.75%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	87.47%	92.38%
CHEMBL1907	P15144	Aminopeptidase N	86.75%	93.31%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	84.59%	96.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	84.34%	95.53%
CHEMBL3401	O75469	Pregnane X receptor	82.04%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.70%	99.23%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	81.41%	82.67%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.27%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.06%	96.21%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.89%	90.95%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.87%	94.03%
CHEMBL5543	Q9Y463	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	80.58%	94.70%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.48%	85.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.47%	96.09%

Plants that contains it

• Euphorbia franckiana
• Geranium nepalense
• Grindelia ciliata
• Haplophyllum bucharicum
• Haplophyllum cappadocicum
• Haplophyllum dauricum
• Haplophyllum patavinum
• Haplophyllum tuberculatum
• Hertia intermedia
• Justicia procumbens
• Kippistia suaedifolia
• Linum austriacum
• Linum leonii
• Linum perenne
• Pelargonium reniforme
• Phyllanthus acuminatus
• Phyllanthus anisolobus
• Polygala amarella
• Sesbania drummondii
• Swertia angustifolia

Cross-Links

• PubChem: 442882
• NPASS: NPC299820
• LOTUS: LTS0069069
• wikiData: Q27107062