2,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indol-1-one

Details

• Internal ID: 428493dc-971b-41d0-8a81-f2913b5eb737
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
• InChI: InChI=1S/C11H10N2O/c14-11-10-8(5-6-12-11)7-3-1-2-4-9(7)13-10/h1-4,13H,5-6H2,(H,12,14)
• InChI Key: FZHZQHNKCPJTNQ-UHFFFAOYSA-N
• Popularity: 20 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₀N₂O
• Molecular Weight: 186.21 g/mol
• Exact Mass: 186.079312947 g/mol
• Topological Polar Surface Area (TPSA): 44.90 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 1
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-one
• 2,3,4,9-tetrahydropyrido[3,4-b]indol-1-one
• 2,3,4,9-Tetrahydro-1H-pyrido(3,4-b)indol-1-one
• DTXSID50170823
• 2,3,4,9-tetrahydropyrido(3,4-b)indol-1-one
• RefChem:1059200
• DTXCID8093314
• 241-878-7
• L-Oxonoreleagnine
• 1H-Pyrido[3,4-b]indol-1-one, 2,3,4,9-tetrahydro-
• 1,2,3,4-Tetrahydronorharman-1-one
• MFCD00065240
• 2,3,4,9-Tetrahydro-1H-beta-carbolin-1-one
• 2,3,4,9-Tetrahydro-beta-carbolin-1-one
• MLS000766137
• 1H,2H,3H,4H,9H-PYRIDO[3,4-B]INDOL-1-ONE
• 2,3,4-trihydrobeta-carbolin-1-one
• SMR000122646
• EINECS 241-878-7
• NSC147829
• 1H-Pyrido[3,4-b]indol-1-one,2,3,4,9-tetrahydro-
• Oprea1_215891
• Oprea1_286796
• MLS000523573
• MLS001049054
• SCHEMBL797563
• CHEMBL444810
• orb1297037
• SCHEMBL2882593
• 1,3,4-Tetrahydronorharman-1-one
• HMS2357J05
• SAA95282
• AC4806
• SBB002123
• STK698945
• STL565918
• 4,9-dihydro-3H-beta-carbolin-1-ol
• AKOS005521452
• AKOS037623635
• HY-W268334
• NSC 147829
• NSC-147829
• 1H-Pyrido[3, 2,3,4,9-tetrahydro-
• NCGC00245519-01
• NCGC00245519-02
• AS-67700
• ST077037
• SY246488
• 1-oxo-1,2,3,4-tetrahydro-beta-carboline
• 1,2,3,4-Tetrahydro-1-oxo-beta-carboline
• 1,3,4-Tetrahydro-1-oxo-.beta.-carboline
• DB-148669
• CS-0313669
• NS00025910
• 1,2,3,4-Tetrahydro-1-oxo-.beta.-carboline
• 2,3,4,9-Tetrahydro-1H-beta-carbolin-1-one #
• AO-567/14623012
• 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indol-1-one
• InChI=1/C11H10N2O/c14-11-10-8(5-6-12-11)7-3-1-2-4-9(7)13-10/h1-4,13H,5-6H2,(H,12,14

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9920	99.20%
Caco-2	+	0.7591	75.91%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.4969	49.69%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9537	95.37%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.7540	75.40%
P-glycoprotein inhibitior	-	0.9827	98.27%
P-glycoprotein substrate	-	0.9407	94.07%
CYP3A4 substrate	-	0.5445	54.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8418	84.18%
CYP3A4 inhibition	-	0.8267	82.67%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.6481	64.81%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.9150	91.50%
CYP inhibitory promiscuity	-	0.5357	53.57%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7529	75.29%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.7721	77.21%
Skin irritation	-	0.7870	78.70%
Skin corrosion	-	0.9512	95.12%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5606	56.06%
Micronuclear	+	0.6500	65.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.8946	89.46%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.5923	59.23%
Acute Oral Toxicity (c)	III	0.4976	49.76%
Estrogen receptor binding	+	0.5285	52.85%
Androgen receptor binding	+	0.5424	54.24%
Thyroid receptor binding	+	0.5642	56.42%
Glucocorticoid receptor binding	-	0.6923	69.23%
Aromatase binding	+	0.6370	63.70%
PPAR gamma	+	0.7459	74.59%
Honey bee toxicity	-	0.9071	90.71%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	-	0.9136	91.36%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	PMID: 24128115
CHEMBL3356	P05177	Cytochrome P450 1A2	2818.38 nM	AC50	PMID: 22686608
CHEMBL3622	P33261	Cytochrome P450 2C19	15848.93 nM	AC50	PMID: 20112996
CHEMBL5514	P42858	Huntingtin	5011.9 nM	Potency	DOI: 10.1007/s00044-011-9965-x
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM; 31622.8 nM	Potency; Potency	PMID: 9644059; PMID: 26854381

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	97.22%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.22%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.30%	95.56%
CHEMBL255	P29275	Adenosine A2b receptor	93.31%	98.59%
CHEMBL3192	Q9BY41	Histone deacetylase 8	91.87%	93.99%
CHEMBL3310	Q96DB2	Histone deacetylase 11	90.31%	88.56%
CHEMBL2535	P11166	Glucose transporter	89.60%	98.75%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	89.59%	96.00%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	88.53%	92.67%
CHEMBL2581	P07339	Cathepsin D	88.13%	98.95%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	86.20%	81.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.29%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.81%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.25%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.10%	97.09%
CHEMBL5443	O00311	Cell division cycle 7-related protein kinase	81.37%	96.11%
CHEMBL1829	O15379	Histone deacetylase 3	80.50%	95.00%

Plants that contains it

• Trigonostemon bonianus

Cross-Links

• PubChem: 87371
• NPASS: NPC141353
• ChEMBL: CHEMBL444810
• LOTUS: LTS0246489
• wikiData: Q83040834