Pinoline

Details

• Internal ID: e42b7435-9e30-4b73-9aab-d6d68df03f86
• Taxonomy: Organoheterocyclic compounds > Indoles and derivatives > Pyridoindoles > Beta carbolines
• IUPAC Name: 6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• InChI: InChI=1S/C12H14N2O/c1-15-8-2-3-11-10(6-8)9-4-5-13-7-12(9)14-11/h2-3,6,13-14H,4-5,7H2,1H3
• InChI Key: QYMDEOQLJUUNOF-UHFFFAOYSA-N
• Popularity: 158 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₄N₂O
• Molecular Weight: 202.25 g/mol
• Exact Mass: 202.110613074 g/mol
• Topological Polar Surface Area (TPSA): 37.10 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.82
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole
• pinoline
• 6-Methoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole
• 6-methoxytryptoline
• 6-Methoxy-1,2,3,4-tetrahydro-beta-carboline
• 6-MeOthbc
• 6-methoxy-2,3,4,9-tetrahydro-1H-beta-carboline
• 6-Methoxytetrahydro-beta-carboline
• MFCD00012071
• 6-Methoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4b] indole
• 1H-Pyrido[3,4-b]indole, 2,3,4,9-tetrahydro-6-methoxy-
• 2,3,4,9-Tetrahydro-6-methoxy-1H-pyrido(3,4-b)indole
• 6-methoxy-1H,2H,3H,4H,9H-pyrido[3,4-b]indole
• BR3W85U4GS
• CHEMBL266084
• 1H-Pyrido(3,4-b)indole, 2,3,4,9-tetrahydro-6-methoxy-
• 2,3,4,9-Tetrahydro-6-methoxy-1H-pyrido[3,4-b]indole
• BRN 0172873
• Pinolin
• 6-Methoxy-THBC
• 1H-Pyrido[3,4-b]indole,2,3,4,9-tetrahydro-6-methoxy-
• UNII-BR3W85U4GS
• Lopac-291552
• Lopac0_000002
• Oprea1_064448
• 5-23-12-00047 (Beilstein Handbook Reference)
• MLS002153360
• BIDD:GT0432
• SCHEMBL329762
• DTXSID30174203
• HMS2270A22
• HMS3260A05
• AMY11985
• Tox21_500002
• 6-Methoxytetrahydro-.beta.-carboline
• BDBM50136492
• AKOS001588738
• CCG-204098
• CS-W015500
• FS-6502
• LP00002
• SDCCGMLS-0411989.P028
• SDCCGSBI-0049991.P002
• MLS-0411989
• NCGC00014996-01
• NCGC00014996-02
• NCGC00014996-03
• NCGC00014996-04
• NCGC00014996-05
• NCGC00093529-01
• NCGC00093529-02
• NCGC00260687-01
• PD015498
• SMR000112443
• SY045548
• MLS-0411989.P016
• 6-Methoxy-1,2,3,4-tetrahydro-?-carboline
• EU-0034440
• EU-0100002
• FT-0637978
• A26095
• EN300-374268
• 6-Methoxy-1,2,3,4-tetrahydro-.beta.-carboline
• SR-01000075630
• .beta.-Carboline, 1,2,3,4-tetrahydro-6-methoxy-
• J-013209
• Q3905316
• SR-01000075630-1
• Methyl 2,3,4,9-tetrahydro-1H-beta-carbolin-6-yl ether #
• 6-Methoxy-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole, 97%

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.8638	86.38%
Blood Brain Barrier	+	0.8167	81.67%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6210	62.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9350	93.50%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.6892	68.92%
P-glycoprotein inhibitior	-	0.9500	95.00%
P-glycoprotein substrate	-	0.7234	72.34%
CYP3A4 substrate	-	0.5691	56.91%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	+	0.7236	72.36%
CYP3A4 inhibition	-	0.8496	84.96%
CYP2C9 inhibition	-	0.9288	92.88%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	+	0.9106	91.06%
CYP2C8 inhibition	-	0.8914	89.14%
CYP inhibitory promiscuity	-	0.7671	76.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7008	70.08%
Eye corrosion	-	0.9824	98.24%
Eye irritation	-	0.6856	68.56%
Skin irritation	-	0.6592	65.92%
Skin corrosion	-	0.8965	89.65%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4474	44.74%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8766	87.66%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8858	88.58%
Acute Oral Toxicity (c)	III	0.5719	57.19%
Estrogen receptor binding	-	0.5154	51.54%
Androgen receptor binding	+	0.5782	57.82%
Thyroid receptor binding	+	0.6328	63.28%
Glucocorticoid receptor binding	-	0.7138	71.38%
Aromatase binding	+	0.5239	52.39%
PPAR gamma	-	0.5371	53.71%
Honey bee toxicity	-	0.9403	94.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	-	0.7891	78.91%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	79.4 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	5.6 nM	Potency	via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	1.4 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.13%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.22%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.47%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	94.96%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.22%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.16%	95.56%
CHEMBL2535	P11166	Glucose transporter	90.95%	98.75%
CHEMBL4208	P20618	Proteasome component C5	90.90%	90.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.49%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.10%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.68%	92.94%
CHEMBL2581	P07339	Cathepsin D	86.61%	98.95%
CHEMBL1907	P15144	Aminopeptidase N	86.05%	93.31%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	84.92%	93.24%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.89%	92.62%
CHEMBL213	P08588	Beta-1 adrenergic receptor	81.56%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.44%	99.17%
CHEMBL3438	Q05513	Protein kinase C zeta	80.42%	88.48%

Plants that contains it

• Phyllodium pulchellum

Cross-Links

• PubChem: 1868
• LOTUS: LTS0145183
• wikiData: Q3905316