9H-Pyrido[3,4-B]indole

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	ea655620-e960-4f7b-98f5-5a34ed3b0d16
Taxonomy	Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
IUPAC Name	9H-pyrido[3,4-b]indole
SMILES (Canonical)	C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
SMILES (Isomeric)	C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
InChI	InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
InChI Key	AIFRHYZBTHREPW-UHFFFAOYSA-N
Popularity	2,395 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₁H₈N₂
Molecular Weight	168.19 g/mol
Exact Mass	168.068748264 g/mol
Topological Polar Surface Area (TPSA)	28.70 Å²
XlogP	3.20
Atomic LogP (AlogP)	2.72
H-Bond Acceptor	1
H-Bond Donor	1
Rotatable Bonds	0

Synonyms

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Norharman

Norharmane

244-63-3

beta-Carboline

2,9-Diazafluorene

Carbazoline

9H-Beta-carboline

2-Azacarbazole

2H-Pyrido[3,4-b]indole

.beta.-Carboline

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5989	59.89%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6100	61.00%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9596	95.96%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.6654	66.54%
P-glycoprotein inhibitior	-	0.9768	97.68%
P-glycoprotein substrate	-	0.9412	94.12%
CYP3A4 substrate	-	0.6883	68.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7180	71.80%
CYP3A4 inhibition	+	0.5200	52.00%
CYP2C9 inhibition	-	0.7490	74.90%
CYP2C19 inhibition	-	0.6934	69.34%
CYP2D6 inhibition	+	0.7247	72.47%
CYP1A2 inhibition	+	0.9162	91.62%
CYP2C8 inhibition	+	0.7493	74.93%
CYP inhibitory promiscuity	+	0.6519	65.19%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.7005	70.05%
Eye corrosion	-	0.9445	94.45%
Eye irritation	+	0.9883	98.83%
Skin irritation	+	0.6713	67.13%
Skin corrosion	-	0.9208	92.08%
Ames mutagenesis	+	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6579	65.79%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.7146	71.46%
skin sensitisation	-	0.8362	83.62%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.6840	68.40%
Acute Oral Toxicity (c)	III	0.6768	67.68%
Estrogen receptor binding	+	0.7226	72.26%
Androgen receptor binding	-	0.4921	49.21%
Thyroid receptor binding	+	0.6004	60.04%
Glucocorticoid receptor binding	-	0.5444	54.44%
Aromatase binding	+	0.6795	67.95%
PPAR gamma	-	0.5401	54.01%
Honey bee toxicity	-	0.9065	90.65%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.7500	75.00%
Fish aquatic toxicity	-	0.5329	53.29%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	31622.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	35481.3 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90000 nM	IC50	PMID: 22112538
CHEMBL1991	O14920	Inhibitor of nuclear factor kappa B kinase beta subunit	7943.28 nM	Ki	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	28183.8 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1951	P21397	Monoamine oxidase A	260 nM	Ki	via Super-PRED
CHEMBL2039	P27338	Monoamine oxidase B	1200 nM	Ki	PMID: 22071524
CHEMBL4722	O14965	Serine/threonine-protein kinase Aurora-A	15848.93 nM	Ki	via CMAUP
CHEMBL2147	P11309	Serine/threonine-protein kinase PIM1	6309.57 nM	Ki	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	1412.5 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	96.26%	94.62%
CHEMBL255	P29275	Adenosine A2b receptor	95.28%	98.59%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.83%	94.45%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	90.90%	93.24%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.34%	91.11%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	88.70%	85.30%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.19%	96.00%
CHEMBL3310	Q96DB2	Histone deacetylase 11	88.17%	88.56%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	86.80%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.26%	94.08%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	85.35%	96.47%
CHEMBL2535	P11166	Glucose transporter	84.56%	98.75%
CHEMBL308	P06493	Cyclin-dependent kinase 1	84.55%	91.73%
CHEMBL1781	P11387	DNA topoisomerase I	83.92%	97.00%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	82.31%	98.21%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	82.18%	80.96%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.33%	96.09%
CHEMBL2095172	P14867	GABA-A receptor; alpha-1/beta-2/gamma-2	80.30%	92.67%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Ophiorrhiza acuminata

Panax ginseng

Passiflora incarnata

Picrasma quassioides