3H-Indolo(3,2,1-de)(1,5)naphthyridine-2,6-dione, 10-hydroxy-3-methoxy-

Details

• Internal ID: ee6a2dea-8f2f-41b1-97dc-730051a0e9b2
• Taxonomy: Alkaloids and derivatives > Indolonaphthyridine alkaloids
• IUPAC Name: 12-hydroxy-6-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),8,10(15),11,13-hexaene-2,7-dione
• SMILES (Canonical): CON1C2=C3C(=CC1=O)C4=C(N3C(=O)C=C2)C=CC(=C4)O
• SMILES (Isomeric): CON1C2=C3C(=CC1=O)C4=C(N3C(=O)C=C2)C=CC(=C4)O
• InChI: InChI=1S/C15H10N2O4/c1-21-17-12-4-5-13(19)16-11-3-2-8(18)6-9(11)10(15(12)16)7-14(17)20/h2-7,18H,1H3
• InChI Key: MZQIGQOYXJHSQQ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀N₂O₄
• Molecular Weight: 282.25 g/mol
• Exact Mass: 282.06405680 g/mol
• Topological Polar Surface Area (TPSA): 70.10 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 86293-42-7
• CHEMBL509455
• DTXSID00235476
• 2,3-Dihydro-10-hydroxy-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	+	0.9493	94.93%
Caco-2	+	0.7898	78.98%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7282	72.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8961	89.61%
OATP1B3 inhibitior	+	0.9454	94.54%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7627	76.27%
P-glycoprotein inhibitior	-	0.9150	91.50%
P-glycoprotein substrate	-	0.6983	69.83%
CYP3A4 substrate	-	0.5183	51.83%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8407	84.07%
CYP3A4 inhibition	-	0.6886	68.86%
CYP2C9 inhibition	-	0.6505	65.05%
CYP2C19 inhibition	-	0.7264	72.64%
CYP2D6 inhibition	-	0.8863	88.63%
CYP1A2 inhibition	-	0.5581	55.81%
CYP2C8 inhibition	-	0.6100	61.00%
CYP inhibitory promiscuity	-	0.7083	70.83%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.8100	81.00%
Carcinogenicity (trinary)	Non-required	0.4332	43.32%
Eye corrosion	-	0.9859	98.59%
Eye irritation	+	0.7155	71.55%
Skin irritation	-	0.8201	82.01%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8036	80.36%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.5140	51.40%
skin sensitisation	-	0.8912	89.12%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.5708	57.08%
Acute Oral Toxicity (c)	III	0.6400	64.00%
Estrogen receptor binding	+	0.7792	77.92%
Androgen receptor binding	+	0.7072	70.72%
Thyroid receptor binding	+	0.6894	68.94%
Glucocorticoid receptor binding	+	0.8110	81.10%
Aromatase binding	+	0.6831	68.31%
PPAR gamma	-	0.5304	53.04%
Honey bee toxicity	-	0.8633	86.33%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.7224	72.24%

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	97.76%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	97.14%	83.82%
CHEMBL2581	P07339	Cathepsin D	96.79%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.02%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.46%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.70%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.22%	89.00%
CHEMBL2535	P11166	Glucose transporter	82.00%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.36%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.03%	99.15%

Plants that contains it

• Simaba orinocensis

Cross-Links

• PubChem: 158930
• NPASS: NPC33969