6H-Indolo[3,2,1-de][1,5]naphthyridin-6-one, 5-hydroxy-

Details

• Internal ID: d319ef73-4fd4-4e42-9138-f8e890fa3779
• Taxonomy: Alkaloids and derivatives > Indolonaphthyridine alkaloids
• IUPAC Name: 3-hydroxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• SMILES (Canonical): C1=CC=C2C(=C1)C3=C4N2C(=O)C(=CC4=NC=C3)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C3=C4N2C(=O)C(=CC4=NC=C3)O
• InChI: InChI=1S/C14H8N2O2/c17-12-7-10-13-9(5-6-15-10)8-3-1-2-4-11(8)16(13)14(12)18/h1-7,17H
• InChI Key: HOTCTNQHGRFRLK-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₈N₂O₂
• Molecular Weight: 236.22 g/mol
• Exact Mass: 236.058577502 g/mol
• Topological Polar Surface Area (TPSA): 55.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.14
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 64118-73-6
• 5-hydroxy-canthin-6-one
• 6H-Indolo[3,2,1-de][1,5]naphthyridin-6-one, 5-hydroxy-
• 3-hydroxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• CHEMBL3401850
• 5-Hydroxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one
• HOTCTNQHGRFRLK-UHFFFAOYSA-N
• AKOS040761178
• 5-Hydroxy-6H-indolo[3,2,1-de][1,5]naphthyridin-6-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9913	99.13%
Caco-2	+	0.6395	63.95%
Blood Brain Barrier	+	0.8696	86.96%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8080	80.80%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9598	95.98%
OATP1B3 inhibitior	+	0.9474	94.74%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8883	88.83%
BSEP inhibitior	-	0.7275	72.75%
P-glycoprotein inhibitior	-	0.9035	90.35%
P-glycoprotein substrate	-	0.8862	88.62%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	0.6150	61.50%
CYP2D6 substrate	-	0.8707	87.07%
CYP3A4 inhibition	-	0.8745	87.45%
CYP2C9 inhibition	-	0.7001	70.01%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.7388	73.88%
CYP1A2 inhibition	+	0.9602	96.02%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	-	0.5975	59.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6133	61.33%
Eye corrosion	-	0.9917	99.17%
Eye irritation	+	0.8543	85.43%
Skin irritation	-	0.8013	80.13%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8191	81.91%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	+	0.6711	67.11%
skin sensitisation	-	0.8731	87.31%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.6616	66.16%
Acute Oral Toxicity (c)	III	0.4406	44.06%
Estrogen receptor binding	+	0.6071	60.71%
Androgen receptor binding	+	0.5404	54.04%
Thyroid receptor binding	+	0.7743	77.43%
Glucocorticoid receptor binding	+	0.9627	96.27%
Aromatase binding	+	0.8437	84.37%
PPAR gamma	+	0.7833	78.33%
Honey bee toxicity	-	0.9361	93.61%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.6518	65.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	96.31%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.13%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.74%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.49%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.26%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.14%	93.99%
CHEMBL2581	P07339	Cathepsin D	91.20%	98.95%
CHEMBL2535	P11166	Glucose transporter	90.53%	98.75%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	89.95%	96.47%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.98%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.96%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.91%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.27%	93.40%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.01%	94.00%
CHEMBL1781	P11387	DNA topoisomerase I	86.76%	97.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.94%	96.09%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	82.77%	92.67%
CHEMBL1899	P46098	Serotonin 3a (5-HT3a) receptor	82.64%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.59%	94.62%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.23%	93.65%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.15%	93.10%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	80.89%	88.00%
CHEMBL255	P29275	Adenosine A2b receptor	80.38%	98.59%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.13%	97.36%

Plants that contains it

• Ailanthus altissima
• Simarouba amara

Cross-Links

• PubChem: 135735549
• LOTUS: LTS0019113
• wikiData: Q105031524