9-Methoxycanthin-6-one

Details

• Internal ID: baf1bf99-f972-48d2-bdc4-bd2c248b2108
• Taxonomy: Alkaloids and derivatives > Indolonaphthyridine alkaloids
• IUPAC Name: 13-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• SMILES (Canonical): COC1=CC2=C(C=C1)C3=C4N2C(=O)C=CC4=NC=C3
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3=C4N2C(=O)C=CC4=NC=C3
• InChI: InChI=1S/C15H10N2O2/c1-19-9-2-3-10-11-6-7-16-12-4-5-14(18)17(15(11)12)13(10)8-9/h2-8H,1H3
• InChI Key: OWCRARVHWCCRAG-UHFFFAOYSA-N
• Popularity: 21 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀N₂O₂
• Molecular Weight: 250.25 g/mol
• Exact Mass: 250.074227566 g/mol
• Topological Polar Surface Area (TPSA): 44.10 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.45
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 74991-91-6
• 8-Methoxycanthin-6-one
• 9-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one
• CHEBI:66699
• 13-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• 13-methoxy-1,6-diazatetracyclo[7.6.1.0(5,16).0(10,15)]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• CHEMBL504978
• DTXSID90432290
• BCP33217
• ZCA99191
• AKOS037515610
• NCGC00385518-01
• AS-57655
• PD098532
• HY-112642
• CS-0058761
• D93564
• Q27135320
• 13-METHOXY-1,6-DIAZATETRACYCLO[7.6.1.0?,(1)?.0(1)?,(1)?]HEXADECA-3,5,7,9(16),10(15),11,13-HEPTAEN-2-ONE
• 13-methoxy-1,6-diazatetracyclo[7.6.1.0?,??.0??,??]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9963	99.63%
Caco-2	+	0.8729	87.29%
Blood Brain Barrier	+	0.8946	89.46%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8241	82.41%
OATP2B1 inhibitior	-	0.8613	86.13%
OATP1B1 inhibitior	+	0.9627	96.27%
OATP1B3 inhibitior	+	0.9585	95.85%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8348	83.48%
BSEP inhibitior	+	0.6692	66.92%
P-glycoprotein inhibitior	-	0.8338	83.38%
P-glycoprotein substrate	-	0.7204	72.04%
CYP3A4 substrate	+	0.5439	54.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8321	83.21%
CYP3A4 inhibition	+	0.5957	59.57%
CYP2C9 inhibition	-	0.8179	81.79%
CYP2C19 inhibition	+	0.5729	57.29%
CYP2D6 inhibition	-	0.7633	76.33%
CYP1A2 inhibition	+	0.9586	95.86%
CYP2C8 inhibition	+	0.4485	44.85%
CYP inhibitory promiscuity	+	0.5282	52.82%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9423	94.23%
Carcinogenicity (trinary)	Non-required	0.4569	45.69%
Eye corrosion	-	0.9836	98.36%
Eye irritation	+	0.6847	68.47%
Skin irritation	-	0.8452	84.52%
Skin corrosion	-	0.9716	97.16%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5946	59.46%
Micronuclear	+	0.8200	82.00%
Hepatotoxicity	+	0.5303	53.03%
skin sensitisation	-	0.9028	90.28%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.5983	59.83%
Acute Oral Toxicity (c)	III	0.4689	46.89%
Estrogen receptor binding	+	0.8249	82.49%
Androgen receptor binding	+	0.6481	64.81%
Thyroid receptor binding	+	0.7743	77.43%
Glucocorticoid receptor binding	+	0.9439	94.39%
Aromatase binding	+	0.8815	88.15%
PPAR gamma	-	0.4852	48.52%
Honey bee toxicity	-	0.9114	91.14%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	-	0.7401	74.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.88%	96.09%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	93.85%	93.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.97%	94.00%
CHEMBL2581	P07339	Cathepsin D	92.75%	98.95%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	92.54%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.59%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.95%	85.14%
CHEMBL2535	P11166	Glucose transporter	90.93%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.81%	95.56%
CHEMBL4208	P20618	Proteasome component C5	90.68%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.59%	97.36%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.70%	91.11%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	89.57%	92.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.77%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.63%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	88.29%	93.31%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	87.91%	85.30%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.53%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.37%	99.15%
CHEMBL2243	O00519	Anandamide amidohydrolase	87.19%	97.53%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.90%	93.99%
CHEMBL202	P00374	Dihydrofolate reductase	82.81%	89.92%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	82.24%	100.00%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.28%	94.42%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	80.36%	100.00%

Plants that contains it

• Aralidium pinnatifidum
• Bersama swinnyi
• Blainvillea acmella
• Euphorbia resinifera
• Eurycoma harmandiana
• Eurycoma longifolia
• Geigeria schinzii
• Goniothalamus undulatus
• Gymnospermium kiangnanensis
• Helichrysum sutherlandii
• Hemionitis marantae
• Lophocereus marginatus
• Nemuaron vieillardii
• Ophryosporus charua
• Oreomecon radicata
• Pachycereus pringlei
• Picea laxa
• Prosopis kuntzei
• Pteris leptophylla
• Simaba orinocensis
• Stenocereus thurberi
• Vitex negundo

Cross-Links

• PubChem: 9881423
• NPASS: NPC174758
• ChEMBL: CHEMBL504978
• LOTUS: LTS0254425
• wikiData: Q27135320