N-Desmethyl lergotrile

Details

• Internal ID: f35c6043-f2b7-4ed3-9236-10c0c072e053
• Taxonomy: Organoheterocyclic compounds > Quinolines and derivatives > Indoloquinolines
• IUPAC Name: 2-[(6aR,9S)-5-chloro-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]acetonitrile
• InChI: InChI=1S/C16H16ClN3/c17-16-12-7-14-11(6-9(4-5-18)8-19-14)10-2-1-3-13(20-16)15(10)12/h1-3,9,11,14,19-20H,4,6-8H2/t9-,11?,14-/m1/s1
• InChI Key: QSRIXAFISHOVGA-FVNFBUEFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆ClN₃
• Molecular Weight: 285.77 g/mol
• Exact Mass: 285.1032752 g/mol
• Topological Polar Surface Area (TPSA): 51.60 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.35
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• Desmethyl lergotrile
• 56867-81-3
• 2-[(6aR,9S)-5-chloro-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]acetonitrile
• 2-((6aR,9S)-5-chloro-4,6,6a,7,8,9,10,10a-octahydroindolo(4,3-fg)quinolin-9-yl)acetonitrile
• RefChem:163226
• (8 beta)-2-chloroergoline-8-acetonitrile
• DTXSID00972293
• (2-Chloroergolin-8-yl)acetonitrile
• PDSP1_001603
• PDSP2_001587
• (8beta)-2-Chloroergoline-8-acetonitrile

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9902	99.02%
Caco-2	-	0.5480	54.80%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.4052	40.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8967	89.67%
OATP1B3 inhibitior	+	0.9451	94.51%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	+	0.6500	65.00%
BSEP inhibitior	+	0.6051	60.51%
P-glycoprotein inhibitior	-	0.9404	94.04%
P-glycoprotein substrate	-	0.5937	59.37%
CYP3A4 substrate	+	0.6209	62.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5241	52.41%
CYP3A4 inhibition	+	0.5732	57.32%
CYP2C9 inhibition	-	0.5339	53.39%
CYP2C19 inhibition	+	0.5241	52.41%
CYP2D6 inhibition	+	0.5374	53.74%
CYP1A2 inhibition	+	0.7631	76.31%
CYP2C8 inhibition	+	0.8078	80.78%
CYP inhibitory promiscuity	+	0.7144	71.44%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.7852	78.52%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9982	99.82%
Skin irritation	-	0.7705	77.05%
Skin corrosion	-	0.9215	92.15%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9051	90.51%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.5349	53.49%
skin sensitisation	-	0.8070	80.70%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	+	0.6041	60.41%
Acute Oral Toxicity (c)	III	0.4648	46.48%
Estrogen receptor binding	+	0.8148	81.48%
Androgen receptor binding	+	0.6001	60.01%
Thyroid receptor binding	+	0.6794	67.94%
Glucocorticoid receptor binding	+	0.6008	60.08%
Aromatase binding	+	0.8600	86.00%
PPAR gamma	+	0.6958	69.58%
Honey bee toxicity	-	0.6539	65.39%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.7000	70.00%
Fish aquatic toxicity	+	0.8815	88.15%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3553	P29597	Tyrosine-protein kinase TYK2	97.93%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.84%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.75%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.25%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.68%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.09%	97.09%
CHEMBL1907594	P30926	Neuronal acetylcholine receptor; alpha3/beta4	92.47%	97.23%
CHEMBL3227	P41594	Metabotropic glutamate receptor 5	92.31%	96.42%
CHEMBL2535	P11166	Glucose transporter	91.15%	98.75%
CHEMBL228	P31645	Serotonin transporter	90.56%	95.51%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.27%	94.08%
CHEMBL240	Q12809	HERG	90.09%	89.76%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	89.30%	89.32%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.54%	93.99%
CHEMBL226	P30542	Adenosine A1 receptor	88.45%	95.93%
CHEMBL2581	P07339	Cathepsin D	88.29%	98.95%
CHEMBL3920	Q04759	Protein kinase C theta	86.93%	97.69%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	86.84%	85.30%
CHEMBL2996	Q05655	Protein kinase C delta	86.25%	97.79%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.31%	92.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.06%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.80%	86.92%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	84.75%	89.62%
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	84.64%	94.55%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.13%	97.21%
CHEMBL3310	Q96DB2	Histone deacetylase 11	83.99%	88.56%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	83.82%	80.96%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.80%	91.71%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.57%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.17%	95.89%
CHEMBL1978	P11511	Cytochrome P450 19A1	80.72%	91.76%
CHEMBL222	P23975	Norepinephrine transporter	80.44%	96.06%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.43%	86.33%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	80.12%	93.24%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 194029
• LOTUS: LTS0030433
• wikiData: Q82956033