3-(4-methoxy-9H-pyrido[3,4-b]indol-1-yl)-1-(9H-pyrido[3,4-b]indol-1-yl)propan-1-one

Details

• Internal ID: ff446e2b-d9af-4990-ad01-0458a7cbdd81
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 3-(4-methoxy-9H-pyrido[3,4-b]indol-1-yl)-1-(9H-pyrido[3,4-b]indol-1-yl)propan-1-one
• SMILES (Canonical): COC1=CN=C(C2=C1C3=CC=CC=C3N2)CCC(=O)C4=NC=CC5=C4NC6=CC=CC=C56
• SMILES (Isomeric): COC1=CN=C(C2=C1C3=CC=CC=C3N2)CCC(=O)C4=NC=CC5=C4NC6=CC=CC=C56
• InChI: InChI=1S/C26H20N4O2/c1-32-22-14-28-20(25-23(22)17-7-3-5-9-19(17)30-25)10-11-21(31)26-24-16(12-13-27-26)15-6-2-4-8-18(15)29-24/h2-9,12-14,29-30H,10-11H2,1H3
• InChI Key: TYVAUNQMLMRDBO-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₀N₄O₂
• Molecular Weight: 420.50 g/mol
• Exact Mass: 420.15862589 g/mol
• Topological Polar Surface Area (TPSA): 83.70 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 5.57
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9973	99.73%
Caco-2	-	0.6888	68.88%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.9096	90.96%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.8894	88.94%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	+	0.6183	61.83%
BSEP inhibitior	+	0.9751	97.51%
P-glycoprotein inhibitior	+	0.8453	84.53%
P-glycoprotein substrate	+	0.5948	59.48%
CYP3A4 substrate	+	0.6463	64.63%
CYP2C9 substrate	-	0.5735	57.35%
CYP2D6 substrate	-	0.7804	78.04%
CYP3A4 inhibition	+	0.5000	50.00%
CYP2C9 inhibition	-	0.6778	67.78%
CYP2C19 inhibition	+	0.6258	62.58%
CYP2D6 inhibition	-	0.5580	55.80%
CYP1A2 inhibition	+	0.7953	79.53%
CYP2C8 inhibition	+	0.8662	86.62%
CYP inhibitory promiscuity	+	0.8555	85.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5973	59.73%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9649	96.49%
Skin irritation	-	0.8360	83.60%
Skin corrosion	-	0.9479	94.79%
Ames mutagenesis	+	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7234	72.34%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.5773	57.73%
skin sensitisation	-	0.9061	90.61%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8055	80.55%
Acute Oral Toxicity (c)	III	0.7141	71.41%
Estrogen receptor binding	+	0.9122	91.22%
Androgen receptor binding	+	0.7381	73.81%
Thyroid receptor binding	+	0.6977	69.77%
Glucocorticoid receptor binding	+	0.8494	84.94%
Aromatase binding	+	0.6578	65.78%
PPAR gamma	+	0.8204	82.04%
Honey bee toxicity	-	0.7805	78.05%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5849	58.49%
Fish aquatic toxicity	-	0.9211	92.11%

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	99.06%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.66%	85.14%
CHEMBL255	P29275	Adenosine A2b receptor	92.75%	98.59%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.64%	91.11%
CHEMBL2535	P11166	Glucose transporter	91.77%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.16%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.38%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.26%	99.17%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.69%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.78%	95.56%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	87.04%	92.67%
CHEMBL1781	P11387	DNA topoisomerase I	86.93%	97.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.06%	99.23%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.80%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.76%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.73%	94.45%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	85.11%	96.00%
CHEMBL2581	P07339	Cathepsin D	84.86%	98.95%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	84.45%	93.24%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.36%	96.00%
CHEMBL4208	P20618	Proteasome component C5	83.89%	90.00%
CHEMBL1907	P15144	Aminopeptidase N	83.26%	93.31%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.32%	95.50%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.30%	94.62%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	81.53%	92.29%
CHEMBL1287628	Q9Y5S8	NADPH oxidase 1	81.49%	95.48%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.37%	92.62%

Plants that contains it

• Picrasma quassioides

Cross-Links

• PubChem: 25261268
• LOTUS: LTS0084025
• wikiData: Q105267749