3H-Indolo(3,2,1-de)(1,5)naphthyridine-2,6-dione, 3-methoxy-

Details

• Internal ID: 2d5659c8-fc1d-4a46-bb08-8cc8a4b5eadf
• Taxonomy: Alkaloids and derivatives > Indolonaphthyridine alkaloids
• IUPAC Name: 6-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),8,10,12,14-hexaene-2,7-dione
• SMILES (Canonical): CON1C2=C3C(=CC1=O)C4=CC=CC=C4N3C(=O)C=C2
• SMILES (Isomeric): CON1C2=C3C(=CC1=O)C4=CC=CC=C4N3C(=O)C=C2
• InChI: InChI=1S/C15H10N2O3/c1-20-17-12-6-7-13(18)16-11-5-3-2-4-9(11)10(15(12)16)8-14(17)19/h2-8H,1H3
• InChI Key: MGZZRRUKOPHKBA-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀N₂O₃
• Molecular Weight: 266.25 g/mol
• Exact Mass: 266.06914219 g/mol
• Topological Polar Surface Area (TPSA): 49.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• 74991-92-7
• C15H10N2O3
• 3-methoxycanthin-2,6-dione
• CHEMBL454831
• DTXSID80225951
• 2,3-Dihydro-3-methoxy-6H-indolo[3,2,1-de][1,5]naphthyridine-2,6-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9860	98.60%
Caco-2	+	0.8857	88.57%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7938	79.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9386	93.86%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9069	90.69%
BSEP inhibitior	-	0.6284	62.84%
P-glycoprotein inhibitior	-	0.8758	87.58%
P-glycoprotein substrate	-	0.8185	81.85%
CYP3A4 substrate	+	0.5115	51.15%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8460	84.60%
CYP3A4 inhibition	-	0.6953	69.53%
CYP2C9 inhibition	-	0.6775	67.75%
CYP2C19 inhibition	-	0.5989	59.89%
CYP2D6 inhibition	-	0.8905	89.05%
CYP1A2 inhibition	+	0.6831	68.31%
CYP2C8 inhibition	-	0.7586	75.86%
CYP inhibitory promiscuity	-	0.5541	55.41%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8300	83.00%
Carcinogenicity (trinary)	Non-required	0.4454	44.54%
Eye corrosion	-	0.9831	98.31%
Eye irritation	+	0.6013	60.13%
Skin irritation	-	0.8240	82.40%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	+	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6938	69.38%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	+	0.6054	60.54%
skin sensitisation	-	0.8749	87.49%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.5805	58.05%
Acute Oral Toxicity (c)	III	0.6594	65.94%
Estrogen receptor binding	+	0.7916	79.16%
Androgen receptor binding	+	0.6714	67.14%
Thyroid receptor binding	+	0.6829	68.29%
Glucocorticoid receptor binding	+	0.7766	77.66%
Aromatase binding	+	0.6705	67.05%
PPAR gamma	-	0.7393	73.93%
Honey bee toxicity	-	0.8167	81.67%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6500	65.00%
Fish aquatic toxicity	+	0.8188	81.88%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.00%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.57%	95.56%
CHEMBL2581	P07339	Cathepsin D	96.03%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.60%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.98%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.86%	93.99%
CHEMBL4040	P28482	MAP kinase ERK2	87.27%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.80%	96.09%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	85.52%	92.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.50%	89.00%
CHEMBL2535	P11166	Glucose transporter	83.68%	98.75%
CHEMBL1907	P15144	Aminopeptidase N	80.20%	93.31%

Plants that contains it

• Simaba orinocensis

Cross-Links

• PubChem: 156537
• NPASS: NPC277157
• LOTUS: LTS0083079
• wikiData: Q83105160