1-Hydroxy-9-medroxycanthin-6-one

Details

• Internal ID: 06d4cb8f-4ca0-4591-aaee-3888989c3b2f
• Taxonomy: Alkaloids and derivatives > Indolonaphthyridine alkaloids
• IUPAC Name: 8-hydroxy-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=C3O
• SMILES (Isomeric): COC1=CC2=C(C=C1)C3=C4N2C(=O)C=CC4=NC=C3O
• InChI: InChI=1S/C15H10N2O3/c1-20-8-2-3-9-11(6-8)17-13(19)5-4-10-15(17)14(9)12(18)7-16-10/h2-7,18H,1H3
• InChI Key: KFHGYFDVGYKREV-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): 64.40 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.15
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 622408-85-9
• 8-hydroxy-13-methoxy-1,6-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-3,5(16),6,8,10,12,14-heptaen-2-one
• 1-Hydroxy-9-methoxycanthin-6-one
• AKOS040760883

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9907	99.07%
Caco-2	+	0.8099	80.99%
Blood Brain Barrier	+	0.7317	73.17%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7894	78.94%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9445	94.45%
OATP1B3 inhibitior	+	0.9562	95.62%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.5688	56.88%
P-glycoprotein inhibitior	-	0.8284	82.84%
P-glycoprotein substrate	-	0.7916	79.16%
CYP3A4 substrate	+	0.5674	56.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	+	0.7005	70.05%
CYP2C9 inhibition	-	0.7949	79.49%
CYP2C19 inhibition	-	0.5250	52.50%
CYP2D6 inhibition	-	0.8005	80.05%
CYP1A2 inhibition	+	0.9147	91.47%
CYP2C8 inhibition	+	0.5478	54.78%
CYP inhibitory promiscuity	-	0.5984	59.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9323	93.23%
Carcinogenicity (trinary)	Non-required	0.5350	53.50%
Eye corrosion	-	0.9891	98.91%
Eye irritation	+	0.6667	66.67%
Skin irritation	-	0.8427	84.27%
Skin corrosion	-	0.9731	97.31%
Ames mutagenesis	+	0.7336	73.36%
Human Ether-a-go-go-Related Gene inhibition	-	0.6637	66.37%
Micronuclear	+	0.8500	85.00%
Hepatotoxicity	+	0.6139	61.39%
skin sensitisation	-	0.9226	92.26%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.6323	63.23%
Acute Oral Toxicity (c)	III	0.5953	59.53%
Estrogen receptor binding	+	0.8044	80.44%
Androgen receptor binding	+	0.6024	60.24%
Thyroid receptor binding	+	0.7901	79.01%
Glucocorticoid receptor binding	+	0.9550	95.50%
Aromatase binding	+	0.8371	83.71%
PPAR gamma	+	0.7565	75.65%
Honey bee toxicity	-	0.9052	90.52%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	-	0.7694	76.94%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	96.55%	93.24%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.59%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.19%	99.15%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	95.10%	85.30%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.59%	95.56%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.73%	93.99%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.59%	96.09%
CHEMBL4208	P20618	Proteasome component C5	93.15%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.06%	97.36%
CHEMBL2535	P11166	Glucose transporter	92.53%	98.75%
CHEMBL2581	P07339	Cathepsin D	92.11%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.01%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.21%	86.33%
CHEMBL2243	O00519	Anandamide amidohydrolase	90.96%	97.53%
CHEMBL1951	P21397	Monoamine oxidase A	90.60%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.93%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.99%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	88.35%	93.10%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.01%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.19%	94.45%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.89%	93.65%
CHEMBL1907	P15144	Aminopeptidase N	85.62%	93.31%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	84.40%	94.42%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	84.08%	92.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.05%	99.17%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	80.82%	96.47%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.21%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.07%	99.23%

Plants that contains it

• Aralidium pinnatifidum
• Bersama swinnyi
• Blainvillea acmella
• Euphorbia resinifera
• 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
• Stenocereus thurberi
• Vitex negundo

Cross-Links

• PubChem: 11448499
• NPASS: NPC238006
• LOTUS: LTS0261774
• wikiData: Q105140374