1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone

Details

• Internal ID: 2a267a5a-4a9c-49ff-8139-88107fe0326f
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Pyrrolidinylpyridines
• IUPAC Name: 1-methyl-5-pyridin-3-ylpyrrolidin-2-one
• SMILES (Canonical): CN1C(CCC1=O)C2=CN=CC=C2
• SMILES (Isomeric): CN1C(CCC1=O)C2=CN=CC=C2
• InChI: InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3
• InChI Key: UIKROCXWUNQSPJ-UHFFFAOYSA-N
• Popularity: 80 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₂O
• Molecular Weight: 176.21 g/mol
• Exact Mass: 176.094963011 g/mol
• Topological Polar Surface Area (TPSA): 33.20 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• rac Cotinine
• 1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone
• rac-Cotinine
• 1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one
• 1-methyl-5-pyridin-3-ylpyrrolidin-2-one
• 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-
• CHEMBL664
• S-(-)-Cotinine
• CONTININE-2,4,5,6-D4 (PYRIDINE-D4)
• 350818-68-7
• 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (S)-
• 66269-66-7
• (+/-)-Cotinine
• MFCD00077696
• NCGC00093739-04
• (-)-Cotinine;(S)-Cotinine;NIH-10498
• SCHEMBL49061
• DTXSID6047577
• BDBM82069
• CHEBI:182609
• UIKROCXWUNQSPJ-UHFFFAOYSA-N
• HMS3370B20
• HMS3393A15
• COTININE(15% OF THE DOSE)
• CAS_21906
• NSC_21906
• AKOS026750058
• PB32127
• SB10317
• NCGC00015249-02
• NCGC00015249-03
• NCGC00093739-01
• NCGC00093739-02
• NCGC00093739-03
• NCGC00093739-05
• NCGC00093739-06
• NCGC00093739-07
• NCGC00093739-09
• NCGC00093739-10
• NCGC00094632-01
• NCGC00094632-02
• BP-21994
• LS-13784
• FT-0624074
• FT-0665181
• FT-0665182
• FT-0665183
• FT-0665184
• FT-0695369
• J-009215

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9872	98.72%
Caco-2	+	0.8222	82.22%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7328	73.28%
OATP2B1 inhibitior	-	0.8685	86.85%
OATP1B1 inhibitior	+	0.9699	96.99%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.7923	79.23%
P-glycoprotein inhibitior	-	0.9961	99.61%
P-glycoprotein substrate	-	0.8953	89.53%
CYP3A4 substrate	-	0.6545	65.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8346	83.46%
CYP3A4 inhibition	-	0.9169	91.69%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9099	90.99%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.8837	88.37%
CYP inhibitory promiscuity	-	0.8746	87.46%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6720	67.20%
Eye corrosion	-	0.9825	98.25%
Eye irritation	-	0.6586	65.86%
Skin irritation	-	0.6294	62.94%
Skin corrosion	-	0.7919	79.19%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5806	58.06%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.7375	73.75%
skin sensitisation	-	0.8802	88.02%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7462	74.62%
Nephrotoxicity	-	0.6640	66.40%
Acute Oral Toxicity (c)	III	0.5619	56.19%
Estrogen receptor binding	-	0.9190	91.90%
Androgen receptor binding	-	0.8511	85.11%
Thyroid receptor binding	-	0.8099	80.99%
Glucocorticoid receptor binding	-	0.5473	54.73%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.5665	56.65%
Honey bee toxicity	-	0.9724	97.24%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.9207	92.07%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	5 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	0.9 nM	Potency	via Super-PRED
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	25.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.28%	96.09%
CHEMBL2581	P07339	Cathepsin D	94.16%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	92.89%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.94%	95.56%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	84.84%	93.65%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.83%	86.33%
CHEMBL1907589	P17787	Neuronal acetylcholine receptor; alpha4/beta2	83.76%	94.55%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.58%	97.09%
CHEMBL1902	P62942	FK506-binding protein 1A	81.23%	97.05%
CHEMBL255	P29275	Adenosine A2b receptor	81.15%	98.59%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.90%	95.89%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	80.32%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.31%	99.23%

Plants that contains it

• Haloxylon persicum
• Nicotiana alata
• Nicotiana tabacum

Cross-Links

• PubChem: 408
• LOTUS: LTS0002099
• wikiData: Q81984445