Chaihunaphthone

Details

• Internal ID: ab18c8c2-c913-4042-a476-e11f557aee2c
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 4-(1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
• InChI: InChI=1S/C22H18O7/c1-24-17-8-12-6-13-14(9-27-22(13)23)18(19(12)21(26-3)20(17)25-2)11-4-5-15-16(7-11)29-10-28-15/h4-8H,9-10H2,1-3H3
• InChI Key: GVORHOLLLQETHK-UHFFFAOYSA-N
• Popularity: 2 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): 72.50 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.93
• H-Bond Acceptor: 7
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• 6258-43-1
• NSC 283809
• 89YU6S2X17
• UNII-89YU6S2X17
• 4-(1,3-Benzodioxol-5-yl)-5,6,7-trimethoxynaphtho[2,3-c]furan-1(3H)-one
• NSC-283809
• 4-(1,3-Benzodioxol-5-yl)-5,6,7-trimethoxynaphtho(2,3-c)furan-1(3H)-one
• DTXSID20211616
• 4-(1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
• NAPHTHO(2,3-C)FURAN-1(3H)-ONE, 5,6,7-TRIMETHOXY-4-(3,4-(METHYLENEDIOXY)PHENYL)-
• 4-(1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3H-benzo(f)(2)benzofuran-1-one
• RefChem:124977
• DTXCID50134107
• NSC283809
• Naphtho(2,3-c)furan-1(3H)-one, 4-(1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-
• SCHEMBL14252990
• DS-005001
• 4-(1,3-benzodioxol-5-yl)-5,6,7-trimethoxy-3H-benzo[f]isobenzofuran-1-one
• 4-(Benzo[d][1,3]dioxol-5-yl)-5,6,7-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	+	0.8339	83.39%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7177	71.77%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9378	93.78%
OATP1B3 inhibitior	+	0.9697	96.97%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9617	96.17%
P-glycoprotein inhibitior	+	0.7282	72.82%
P-glycoprotein substrate	-	0.8722	87.22%
CYP3A4 substrate	+	0.5972	59.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8360	83.60%
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	+	0.5689	56.89%
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	-	0.7603	76.03%
Skin irritation	-	0.8279	82.79%
Skin corrosion	-	0.9728	97.28%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4790	47.90%
Micronuclear	+	0.7974	79.74%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.6784	67.84%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.6923	69.23%
Acute Oral Toxicity (c)	III	0.6311	63.11%
Estrogen receptor binding	+	0.9090	90.90%
Androgen receptor binding	+	0.6479	64.79%
Thyroid receptor binding	+	0.7056	70.56%
Glucocorticoid receptor binding	+	0.9477	94.77%
Aromatase binding	+	0.5972	59.72%
PPAR gamma	+	0.6971	69.71%
Honey bee toxicity	-	0.8105	81.05%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
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
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.83%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.21%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.33%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.23%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.56%	94.80%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.35%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.20%	94.45%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	92.55%	80.96%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.52%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.95%	92.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.47%	91.11%
CHEMBL240	Q12809	HERG	90.07%	89.76%
CHEMBL2535	P11166	Glucose transporter	90.01%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	87.75%	92.98%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	87.50%	95.53%
CHEMBL1907	P15144	Aminopeptidase N	87.42%	93.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.09%	96.09%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	85.91%	96.09%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	85.84%	85.00%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	84.74%	81.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.31%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.27%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.74%	89.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.65%	82.67%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.44%	80.78%
CHEMBL5747	Q92793	CREB-binding protein	82.47%	95.12%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.21%	99.23%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.10%	95.78%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.93%	96.67%
CHEMBL4208	P20618	Proteasome component C5	80.92%	90.00%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	80.84%	94.03%
CHEMBL3438	Q05513	Protein kinase C zeta	80.47%	88.48%

Plants that contains it

• Bupleurum scorzonerifolium

Cross-Links

• PubChem: 323456
• NPASS: NPC141116
• LOTUS: LTS0258343
• wikiData: Q83086583