ID: ALA12543

Max Phase: Phase

Molecular Formula: C5H9NO

Molecular Weight: 99.13

Molecule Type: Small molecule

Representations

Synonyms (5): Methyl pyrrolidone | Methylpyrrolidone | N-Methyl Pyrrolidinone | N-methyl-pyrrolidone | NSC-4594
Synonyms from Alternative Forms(5):

Canonical SMILES:  CN1CCCC1=O

Standard InChI:  InChI=1S/C5H9NO/c1-6-4-2-3-5(6)7/h2-4H2,1H3

Standard InChI Key:  SECXISVLQFMRJM-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 99.13

Molecular Weight (Monoisotopic): 99.0684

AlogP: 0.24

#Rotatable Bonds: 0

Polar Surface Area: 20.31

Molecular Species: NEUTRAL

HBA: 1

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: -0.36

CX LogD: -0.36

Aromatic Rings: 0

Heavy Atoms: 7

QED Weighted: 0.43

Np Likeness Score: -0.70

References

1. Li C, Schwartz EL, Mella SL, Rittmann LS, Sartorelli AC..  (1981)  Induction of differentiation of leukemia cells in vitro by N-substituted amides, lactams, and 2-pyridones.,  24  (9): [PMID:6945436] [10.1021/jm00141a016]

2. Sykes NO, Macdonald SJ, Page MI..  (2002)  Acylating agents as enzyme inhibitors and understanding their reactivity for drug design.,  45  (13): [PMID:12061887] [10.1021/jm0111245]

3. Chen JJ, Yang CS, Peng CF, Chen IS, Miaw CL..  (2008)  Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica.,  71  (6): [PMID:18471021] [10.1021/np800097t]

4. Hewings DS, Wang M, Philpott M, Fedorov O, Uttarkar S, Filippakopoulos P, Picaud S, Vuppusetty C, Marsden B, Knapp S, Conway SJ, Heightman TD..  (2011)  3,5-dimethylisoxazoles act as acetyl-lysine-mimetic bromodomain ligands.,  54  (19): [PMID:21851057] [10.1021/jm200640v]

5. Chung CW, Dean AW, Woolven JM, Bamborough P..  (2012)  Fragment-based discovery of bromodomain inhibitors part 1: inhibitor binding modes and implications for lead discovery.,  55  (2): [PMID:22136404] [10.1021/jm201320w]

6. Muller S, Knapp S.  (2014)  Discovery of BET bromodomain inhibitors and their role in target validation,  5  (3): [10.1039/C3MD00291H]

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. Micewicz ED, Khachatoorian R, French SW, Ruchala P..  (2018)  Identification of novel small-molecule inhibitors of Zika virus infection.,  28  (3): [PMID:29258771] [10.1016/j.bmcl.2017.12.019]

10. Unpublished dataset, 

11. Hilton-Proctor JP, Ilyichova O, Zheng Z, Jennings IG, Johnstone RW, Shortt J, Mountford SJ, Scanlon MJ, Thompson PE..  (2019)  Synthesis and elaboration of N-methylpyrrolidone as an acetamide fragment substitute in bromodomain inhibition.,  27  (24): [PMID:31727451] [10.1016/j.bmc.2019.115157]

12. Vaidergorn MM, da Silva Emery F, Ganesan A..  (2021)  From Hit Seeking to Magic Bullets: The Successful Union of Epigenetic and Fragment Based Drug Discovery (EPIDD + FBDD).,  64  (19.0): [PMID:34591474] [10.1021/acs.jmedchem.1c00787]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates