2-Pyrrolidinone

Details

• Internal ID: d070499f-56c2-4aa4-9a90-e27f5a28f403
• Taxonomy: Organoheterocyclic compounds > Pyrrolidines > Pyrrolidones > Pyrrolidine-2-ones
• IUPAC Name: pyrrolidin-2-one
• SMILES (Canonical): C1CC(=O)NC1
• SMILES (Isomeric): C1CC(=O)NC1
• InChI: InChI=1S/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6)
• InChI Key: HNJBEVLQSNELDL-UHFFFAOYSA-N
• Popularity: 3,346 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄H₇NO
• Molecular Weight: 85.10 g/mol
• Exact Mass: 85.052763847 g/mol
• Topological Polar Surface Area (TPSA): 29.10 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.10
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• 2-Pyrrolidinone
• 616-45-5
• 2-PYRROLIDONE
• Pyrrolidone
• Butyrolactam
• 2-Oxopyrrolidine
• Pyrrolidon
• PYRROLIDINONE
• 2-Ketopyrrolidine
• 2-Pyrol
• gamma-Butyrolactam
• alpha-Pyrrolidinone
• 4-Aminobutyric acid lactam
• gamma-Aminobutyric lactam
• gamma-Aminobutyrolactam
• alpha-Pyrrolidone
• .alpha.-Pyrrolidone
• Pyrrolidon [German]
• 2-Tetrahydropyrrolone
• gamma-Aminobutyric acid lactam
• .gamma.-Aminobutyrolactam
• Butanoic acid, 4-amino-, lactam
• Pyrrolidone-2
• pyrrolid-2-one
• NSC 4593
• NSC 8413
• pyrrolidine-2-one
• azacyclopentan-2-one
• .gamma.-Butyrolactam
• .alpha.-Pyrrolidinone
• HSDB 2652
• EINECS 210-483-1
• UNII-KKL5D39EOL
• KKL5D39EOL
• .gamma.-Aminobutyric lactam
• DTXSID8027246
• CHEBI:36592
• NSC-4593
• NSC-8413
• Butanoic acid, lactam
• LAM
• 2-Pyrrolidinone, 99%
• WLN: T5MVTJ
• 2-PYRROLIDINONE-3,3,4,4,5,5-D6
• EC 210-483-1
• DTXCID707246
• Pyrrolidone (Pyrrolidin-2-one)
• CAS-616-45-5
• MFCD00005270
• butyrolactim
• pyrollidone
• 2pyrrolidinone
• a-pyrrolidone
• 2-pirrolidinona
• 2-pyrollidinone
• 2-pyrolidinone
• 2-pyrrolidinon
• Aminobutyrolactam
• Soluphor P
• pyrrolidin-2-on
• 2-pyrrolidin-one
• pyrolidine-2-one
• pyrollidin-2-one
• Tetrahydropyrrolone
• 2-oxo-pyrrolidine
• Aminobutyric lactam
• 2-Azacyclopentanone
• Pyrrolidinone, 2-
• 2-Oxo-4-butyrolactam
• Aminobutyric acid lactam
• 1-azacyclopentan-2-one
• 2-Pyrrolidone-Butyrolactam
• 2-pyrrolidone for synthesis
• 2-Pyrrolidinone, >=99%
• NCIOpen2_000687
• PYRROLIDONE [MART.]
• 2-PYRROLIDONE [MI]
• 2-PYRROLIDONE [HSDB]
• CHEMBL276849
• FEMA NO. 4829
• .gamma.-Aminobutyric acid lactam
• NSC4593
• NSC8413
• 2-Pyrol4-aminobutyric acid lactam
• PYRROLIDONE [EP MONOGRAPH]
• Pyrrolidin-2-one (2-Pyrrolidone)
• BCP26683
• HY-Y1831
• Tox21_201630
• Tox21_303259
• STL197473
• AKOS000119138
• CS-T-41274
• FG-0424
• 2-PYRROLIDONE MFC4 H7 N1 O1
• NCGC00249089-01
• NCGC00257072-01
• NCGC00259179-01
• 28261-54-3
• PD078398
• POVIDONE IMPURITY B [EP IMPURITY]
• 2-Pyrrolidinone, purum, >=98.0% (GC)
• LS-138586
• Pyrrolidin-2-one (1-aza-2-cyclopentanone)
• CS-0019427
• P0575
• EN300-19119
• A15700
• D96808
• Q285640
• F0001-1634
• Z104472846
• Pyrrolidone, European Pharmacopoeia (EP) Reference Standard
• InChI=1/C4H7NO/c6-4-2-1-3-5-4/h1-3H2,(H,5,6

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9954	99.54%
Caco-2	+	0.6788	67.88%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.8571	85.71%
Subcellular localzation	Lysosomes	0.5486	54.86%
OATP2B1 inhibitior	-	0.8571	85.71%
OATP1B1 inhibitior	+	0.9793	97.93%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.9509	95.09%
P-glycoprotein inhibitior	-	0.9875	98.75%
P-glycoprotein substrate	-	0.9882	98.82%
CYP3A4 substrate	-	0.7696	76.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8335	83.35%
CYP3A4 inhibition	-	0.9941	99.41%
CYP2C9 inhibition	-	0.9374	93.74%
CYP2C19 inhibition	-	0.9309	93.09%
CYP2D6 inhibition	-	0.9092	90.92%
CYP1A2 inhibition	-	0.8031	80.31%
CYP2C8 inhibition	-	0.9978	99.78%
CYP inhibitory promiscuity	-	0.9348	93.48%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.6456	64.56%
Eye corrosion	-	0.6951	69.51%
Eye irritation	+	0.9877	98.77%
Skin irritation	-	0.8722	87.22%
Skin corrosion	-	0.9639	96.39%
Ames mutagenesis	-	0.7178	71.78%
Human Ether-a-go-go-Related Gene inhibition	-	0.7943	79.43%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.9469	94.69%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	+	0.5159	51.59%
Acute Oral Toxicity (c)	II	0.7436	74.36%
Estrogen receptor binding	-	0.9390	93.90%
Androgen receptor binding	-	0.9548	95.48%
Thyroid receptor binding	-	0.8907	89.07%
Glucocorticoid receptor binding	-	0.9337	93.37%
Aromatase binding	-	0.8637	86.37%
PPAR gamma	-	0.8939	89.39%
Honey bee toxicity	-	0.9387	93.87%
Biodegradation	+	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8700	87.00%
Fish aquatic toxicity	-	0.9858	98.58%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4523454	Q9H255	Olfactory receptor 51E2	1.9 nM	EC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	88.24%	98.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.19%	93.99%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.30%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.57%	97.09%
CHEMBL1907598	P05106	Integrin alpha-V/beta-3	83.43%	95.71%
CHEMBL3310	Q96DB2	Histone deacetylase 11	82.07%	88.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.07%	95.56%

Plants that contains it

• Capparis spinosa
• Microtropis japonica
• Panax ginseng
• Panax notoginseng
• Panax quinquefolius
• Vitis vinifera
• Wurfbainia neoaurantiaca

Cross-Links

• PubChem: 12025
• NPASS: NPC145895
• LOTUS: LTS0065626
• wikiData: Q285640