6-methoxy-3,3-dimethyl-12H-pyrano[2,3-c]acridin-7-one

Details

• Internal ID: bb6c0a91-b0d5-44ce-ba0a-529a634cc6fa
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Benzoquinolines > Acridines > Acridones
• IUPAC Name: 6-methoxy-3,3-dimethyl-12H-pyrano[2,3-c]acridin-7-one
• SMILES (Canonical): CC1(C=CC2=C3C(=C(C=C2O1)OC)C(=O)C4=CC=CC=C4N3)C
• SMILES (Isomeric): CC1(C=CC2=C3C(=C(C=C2O1)OC)C(=O)C4=CC=CC=C4N3)C
• InChI: InChI=1S/C19H17NO3/c1-19(2)9-8-12-14(23-19)10-15(22-3)16-17(12)20-13-7-5-4-6-11(13)18(16)21/h4-10H,1-3H3,(H,20,21)
• InChI Key: NEYQKEUFRBPEJP-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₇NO₃
• Molecular Weight: 307.30 g/mol
• Exact Mass: 307.12084340 g/mol
• Topological Polar Surface Area (TPSA): 47.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.87
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 13255-08-8
• 6-methoxy-3,3-dimethyl-12H-pyrano[2,3-c]acridin-7-one
• 3,3-Dimethyl-6-methoxy-3H-pyrano[2,3-c]acridine-7(12H)-one
• De-N-methylacronycine
• des-N-methylacronycine
• CHEMBL454827
• NEYQKEUFRBPEJP-UHFFFAOYSA-N
• 6-methoxy-3,3-dimethyl-3,12-dihydro-7h-pyrano[2,3-c]acridin-7-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.8248	82.48%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6504	65.04%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.9193	91.93%
OATP1B3 inhibitior	+	0.9752	97.52%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9461	94.61%
P-glycoprotein inhibitior	+	0.5869	58.69%
P-glycoprotein substrate	-	0.5897	58.97%
CYP3A4 substrate	+	0.6403	64.03%
CYP2C9 substrate	+	0.5818	58.18%
CYP2D6 substrate	-	0.8280	82.80%
CYP3A4 inhibition	-	0.5494	54.94%
CYP2C9 inhibition	-	0.7154	71.54%
CYP2C19 inhibition	+	0.7807	78.07%
CYP2D6 inhibition	-	0.8144	81.44%
CYP1A2 inhibition	+	0.8576	85.76%
CYP2C8 inhibition	+	0.4736	47.36%
CYP inhibitory promiscuity	+	0.7283	72.83%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Danger	0.5148	51.48%
Eye corrosion	-	0.9883	98.83%
Eye irritation	+	0.7844	78.44%
Skin irritation	-	0.8461	84.61%
Skin corrosion	-	0.9664	96.64%
Ames mutagenesis	+	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3849	38.49%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8510	85.10%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6257	62.57%
Acute Oral Toxicity (c)	III	0.6043	60.43%
Estrogen receptor binding	+	0.9466	94.66%
Androgen receptor binding	+	0.6826	68.26%
Thyroid receptor binding	+	0.8771	87.71%
Glucocorticoid receptor binding	+	0.9120	91.20%
Aromatase binding	+	0.8457	84.57%
PPAR gamma	+	0.8188	81.88%
Honey bee toxicity	-	0.8084	80.84%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.7324	73.24%

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	99.04%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.64%	94.45%
CHEMBL3192	Q9BY41	Histone deacetylase 8	97.52%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.97%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.93%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.90%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.16%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.87%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.75%	94.00%
CHEMBL1937	Q92769	Histone deacetylase 2	91.20%	94.75%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	90.10%	80.96%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	89.32%	81.14%
CHEMBL2535	P11166	Glucose transporter	88.53%	98.75%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.16%	85.30%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.04%	86.33%
CHEMBL1255126	O15151	Protein Mdm4	87.10%	90.20%
CHEMBL255	P29275	Adenosine A2b receptor	86.37%	98.59%
CHEMBL1907	P15144	Aminopeptidase N	86.28%	93.31%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.38%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.02%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.82%	99.23%
CHEMBL4208	P20618	Proteasome component C5	83.46%	90.00%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	83.30%	89.44%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.24%	95.71%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	83.05%	85.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	82.70%	94.80%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.47%	96.67%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	81.17%	92.67%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.80%	85.49%
CHEMBL213	P08588	Beta-1 adrenergic receptor	80.63%	95.56%
CHEMBL325	Q13547	Histone deacetylase 1	80.00%	95.92%

Plants that contains it

• Artemisia capillaris
• Glycosmis mauritiana
• Glycosmis parviflora
• Glycosmis pentaphylla
• Murraya paniculata
• Sarcomelicope dogniensis

Cross-Links

• PubChem: 6325047
• NPASS: NPC241263
• LOTUS: LTS0270532
• wikiData: Q104395349