6-Methoxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4(9),5,7,15,17,19-octaen-14-one

Details

• Internal ID: 25d9a162-4f39-4191-853d-a14d0900acba
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 6-methoxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa-1(21),2(10),4(9),5,7,15,17,19-octaen-14-one
• InChI: InChI=1S/C19H15N3O2/c1-24-11-6-7-12-13-8-9-22-18(17(13)20-16(12)10-11)21-15-5-3-2-4-14(15)19(22)23/h2-7,10,20H,8-9H2,1H3
• InChI Key: POMASUJAYQAJQZ-UHFFFAOYSA-N
• Popularity: 7 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₁₅N₃O₂
• Molecular Weight: 317.30 g/mol
• Exact Mass: 317.116426730 g/mol
• Topological Polar Surface Area (TPSA): 57.70 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• NSC660031
• 11-Methoxyrutecarprine
• BDBM50131049
• NSC-660031
• NCI60_021078
• 11-Methoxy-8,13-dihydro-7H-indolo[2'',3'':3,4]pyrido[2,1-b]quinazolin-5-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.8289	82.89%
Blood Brain Barrier	+	0.8879	88.79%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7942	79.42%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9167	91.67%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	+	0.6428	64.28%
BSEP inhibitior	+	0.8993	89.93%
P-glycoprotein inhibitior	-	0.5164	51.64%
P-glycoprotein substrate	-	0.8288	82.88%
CYP3A4 substrate	+	0.6324	63.24%
CYP2C9 substrate	-	0.7813	78.13%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	+	0.6217	62.17%
CYP2C9 inhibition	-	0.6155	61.55%
CYP2C19 inhibition	-	0.6141	61.41%
CYP2D6 inhibition	-	0.7773	77.73%
CYP1A2 inhibition	+	0.9339	93.39%
CYP2C8 inhibition	+	0.4798	47.98%
CYP inhibitory promiscuity	+	0.7242	72.42%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6377	63.77%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9113	91.13%
Skin irritation	-	0.8259	82.59%
Skin corrosion	-	0.9569	95.69%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5348	53.48%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	+	0.6501	65.01%
skin sensitisation	-	0.9229	92.29%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7176	71.76%
Acute Oral Toxicity (c)	II	0.5811	58.11%
Estrogen receptor binding	+	0.8865	88.65%
Androgen receptor binding	+	0.6824	68.24%
Thyroid receptor binding	+	0.6999	69.99%
Glucocorticoid receptor binding	+	0.8525	85.25%
Aromatase binding	+	0.6350	63.50%
PPAR gamma	+	0.8086	80.86%
Honey bee toxicity	-	0.9016	90.16%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	-	0.8463	84.63%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2231	P04798	Cytochrome P450 1A1	2000 nM	IC50	PMID: 22742761
CHEMBL3356	P05177	Cytochrome P450 1A2	1980 nM	IC50	PMID: 22742761
CHEMBL4878	Q16678	Cytochrome P450 1B1	110 nM; 110 nM	IC50; IC50	PMID: 23632365; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.90%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	96.16%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.07%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.33%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.85%	94.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	94.73%	92.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.44%	93.40%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.02%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.92%	91.11%
CHEMBL3192	Q9BY41	Histone deacetylase 8	93.90%	93.99%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	93.63%	99.23%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	92.43%	96.47%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.37%	86.33%
CHEMBL1781	P11387	DNA topoisomerase I	91.15%	97.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	90.20%	91.71%
CHEMBL2535	P11166	Glucose transporter	89.52%	98.75%
CHEMBL4208	P20618	Proteasome component C5	89.18%	90.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.19%	97.36%
CHEMBL4302	P08183	P-glycoprotein 1	85.65%	92.98%
CHEMBL1907	P15144	Aminopeptidase N	85.16%	93.31%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.08%	96.67%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	83.43%	96.39%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.34%	99.15%
CHEMBL2056	P21728	Dopamine D1 receptor	80.97%	91.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	80.90%	95.53%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	80.46%	85.49%
CHEMBL1913	P09619	Platelet-derived growth factor receptor beta	80.41%	95.70%

Plants that contains it

• Trigonostemon bonianus

Cross-Links

• PubChem: 378228
• NPASS: NPC471762
• ChEMBL: CHEMBL312149
• LOTUS: LTS0025210
• wikiData: Q105212508