Justicidin C

Details

• Internal ID: 2e50e7d2-4330-4611-9f03-324bab739be4
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-1H-benzo[f][2]benzofuran-3-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3COC(=O)C3=C2OC)C4=CC5=C(C=C4)OCO5)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3COC(=O)C3=C2OC)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)20-14(9-27-22(20)23)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3
• InChI Key: RHTTTZYNBXNPSZ-UHFFFAOYSA-N
• Popularity: 40 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

• NEOJUSTICIN B
• 17803-12-2
• UNII-X97477NS3D
• X97477NS3D
• Naphtho(2,3-c)furan-1(3H)-one, 4-(1,3-benzodioxol-5-yl)-6,7,9-trimethoxy-
• Naphtho(2,3-c)furan-1(3H)-one, 6,7,9-trimethoxy-4-(3,4-(methylenedioxy)phenyl)-
• Justicindin A
• Naphtho[2,3-c]furan-1(3H)-one, 4-(1,3-benzodioxol-5-yl)-6,7,9-trimethoxy-
• CHEMBL455623
• SCHEMBL15920775
• DTXSID40170413
• RHTTTZYNBXNPSZ-UHFFFAOYSA-N
• 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-1H-benzo[f][2]benzofuran-3-one
• Q27293719
• 9-(1,3-benzodioxol-5-yl)-4,6,7-trimethoxy-1H-benzo[f]isobenzofuran-3-one
• 4-(benzo[d][1,3]dioxol-5-yl)-6,7,9-trimethoxynaphtho[2,3-c]furan-1(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9911	99.11%
Caco-2	+	0.8921	89.21%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7177	71.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9514	95.14%
OATP1B3 inhibitior	+	0.9697	96.97%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9121	91.21%
P-glycoprotein inhibitior	+	0.8039	80.39%
P-glycoprotein substrate	-	0.8709	87.09%
CYP3A4 substrate	+	0.5666	56.66%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8455	84.55%
CYP3A4 inhibition	+	0.8745	87.45%
CYP2C9 inhibition	+	0.9208	92.08%
CYP2C19 inhibition	+	0.9535	95.35%
CYP2D6 inhibition	-	0.7176	71.76%
CYP1A2 inhibition	-	0.7567	75.67%
CYP2C8 inhibition	+	0.4689	46.89%
CYP inhibitory promiscuity	+	0.9347	93.47%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.3953	39.53%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.6215	62.15%
Skin irritation	-	0.8279	82.79%
Skin corrosion	-	0.9728	97.28%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7557	75.57%
Micronuclear	+	0.7974	79.74%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.6784	67.84%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5145	51.45%
Acute Oral Toxicity (c)	III	0.6311	63.11%
Estrogen receptor binding	+	0.8983	89.83%
Androgen receptor binding	+	0.6822	68.22%
Thyroid receptor binding	+	0.6739	67.39%
Glucocorticoid receptor binding	+	0.9420	94.20%
Aromatase binding	+	0.5357	53.57%
PPAR gamma	+	0.6885	68.85%
Honey bee toxicity	-	0.8315	83.15%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9680	96.80%

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	97.27%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.21%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.82%	94.80%
CHEMBL2581	P07339	Cathepsin D	95.73%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.73%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.97%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.62%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	92.71%	93.31%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	91.87%	92.62%
CHEMBL2535	P11166	Glucose transporter	91.20%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.46%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.75%	89.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	89.67%	80.96%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.77%	85.14%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.60%	82.67%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	84.74%	95.53%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.41%	96.09%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.75%	85.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.65%	97.14%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	82.73%	93.40%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.24%	96.00%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	81.07%	98.21%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.54%	92.38%

Plants that contains it

• Euphorbia franckiana
• Geranium nepalense
• Grindelia ciliata
• Hertia intermedia
• Justicia procumbens
• Kippistia suaedifolia
• Monechma ciliatum
• Pelargonium reniforme
• Polygala amarella
• Swertia angustifolia

Cross-Links

• PubChem: 493173
• NPASS: NPC78944
• LOTUS: LTS0045639
• wikiData: Q27293719