5,6-Methylenedioxy-9-methoxy-7H-dibenzo(de,h)quinoline-7-one

Details

• Internal ID: 8b20d110-d117-4a0c-9e29-99f0c2b5d741
• Taxonomy: Alkaloids and derivatives > Isoaporphines > Oxoisoaporphines
• IUPAC Name: 16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.013,18]icosa-1(20),2(6),7,9,11,13(18),14,16-octaen-19-one
• SMILES (Canonical): COC1=CC2=C(C=C1)C3=NC=CC4=CC5=C(C(=C43)C2=O)OCO5
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3=NC=CC4=CC5=C(C(=C43)C2=O)OCO5
• InChI: InChI=1S/C18H11NO4/c1-21-10-2-3-11-12(7-10)17(20)15-14-9(4-5-19-16(11)14)6-13-18(15)23-8-22-13/h2-7H,8H2,1H3
• InChI Key: BZLSBGPHEXHPAQ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₁NO₄
• Molecular Weight: 305.30 g/mol
• Exact Mass: 305.06880783 g/mol
• Topological Polar Surface Area (TPSA): 57.60 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 5,6-Methylenedioxy-9-methoxy-7H-dibenzo(de,h)quinoline-7-one
• 96681-51-5
• RefChem:119618
• DTXSID40914399
• 12H-Benzo(h)(1,3)benzodioxolo(6,5,4-de)quinolin-12-one, 2-methoxy-
• 2-Methoxy-10H,12H-[1,3]benzodioxolo[6,5,4-de]benzo[h]quinolin-12-one
• 2-Methoxy-12H-benzo(h)(1,3)benzodioxolo(6,5,4-de)quinolin-12-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.8432	84.32%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6020	60.20%
OATP2B1 inhibitior	-	0.8583	85.83%
OATP1B1 inhibitior	+	0.9435	94.35%
OATP1B3 inhibitior	+	0.9703	97.03%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.8123	81.23%
P-glycoprotein inhibitior	-	0.5341	53.41%
P-glycoprotein substrate	-	0.8304	83.04%
CYP3A4 substrate	+	0.5800	58.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7999	79.99%
CYP3A4 inhibition	+	0.9009	90.09%
CYP2C9 inhibition	-	0.5805	58.05%
CYP2C19 inhibition	+	0.8304	83.04%
CYP2D6 inhibition	+	0.6456	64.56%
CYP1A2 inhibition	+	0.9435	94.35%
CYP2C8 inhibition	-	0.5650	56.50%
CYP inhibitory promiscuity	+	0.9013	90.13%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4612	46.12%
Eye corrosion	-	0.9768	97.68%
Eye irritation	-	0.6106	61.06%
Skin irritation	-	0.7796	77.96%
Skin corrosion	-	0.9679	96.79%
Ames mutagenesis	+	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4053	40.53%
Micronuclear	+	0.7374	73.74%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7666	76.66%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.6940	69.40%
Acute Oral Toxicity (c)	III	0.6998	69.98%
Estrogen receptor binding	+	0.9324	93.24%
Androgen receptor binding	+	0.7956	79.56%
Thyroid receptor binding	+	0.8426	84.26%
Glucocorticoid receptor binding	+	0.9225	92.25%
Aromatase binding	+	0.8163	81.63%
PPAR gamma	+	0.8186	81.86%
Honey bee toxicity	-	0.7999	79.99%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.4503	45.03%

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	98.37%	96.77%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	97.28%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	96.77%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.21%	91.11%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	94.30%	85.30%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	93.54%	96.09%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	93.23%	96.67%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.61%	86.33%
CHEMBL2581	P07339	Cathepsin D	91.47%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	91.35%	94.80%
CHEMBL2039	P27338	Monoamine oxidase B	90.82%	92.51%
CHEMBL4040	P28482	MAP kinase ERK2	90.65%	83.82%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.63%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.37%	96.09%
CHEMBL4208	P20618	Proteasome component C5	89.18%	90.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	88.71%	82.67%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.65%	96.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.56%	93.10%
CHEMBL5747	Q92793	CREB-binding protein	88.39%	95.12%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.32%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.18%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.74%	99.15%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	87.64%	94.42%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	87.49%	80.96%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.31%	95.56%
CHEMBL1907	P15144	Aminopeptidase N	87.23%	93.31%
CHEMBL3401	O75469	Pregnane X receptor	85.40%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.16%	92.62%
CHEMBL2243	O00519	Anandamide amidohydrolase	84.43%	97.53%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.66%	100.00%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	81.65%	93.24%
CHEMBL308	P06493	Cyclin-dependent kinase 1	80.99%	91.73%

Plants that contains it

• Menispermum dauricum

Cross-Links

• PubChem: 126022
• NPASS: NPC224192