(S)-N-(2-oxoazetidin-3-yl)nonanamide

ID: ALA3770509

Chembl Id: CHEMBL3770509

PubChem CID: 81689844

Max Phase: Preclinical

Molecular Formula: C12H22N2O2

Molecular Weight: 226.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCC(=O)N[C@H]1CNC1=O

Standard InChI:  InChI=1S/C12H22N2O2/c1-2-3-4-5-6-7-8-11(15)14-10-9-13-12(10)16/h10H,2-9H2,1H3,(H,13,16)(H,14,15)/t10-/m0/s1

Standard InChI Key:  WIDAPGAIOCAZMY-JTQLQIEISA-N

Alternative Forms

1. Parent:

   

   ALA3770509

   N-[(3S)-2-oxoazetidin-3-yl]-nonanamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 226.32

Molecular Weight (Monoisotopic): 226.1681

AlogP: 1.35

#Rotatable Bonds: 8

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.87

CX Basic pKa: ┄

CX LogP: 1.50

CX LogD: 1.50

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.48

Np Likeness Score: 0.15

References

1. Nuzzi A, Fiasella A, Ortega JA, Pagliuca C, Ponzano S, Pizzirani D, Bertozzi SM, Ottonello G, Tarozzo G, Reggiani A, Bandiera T, Bertozzi F, Piomelli D..  (2016)  Potent α-amino-β-lactam carbamic acid ester as NAAA inhibitors. Synthesis and structure-activity relationship (SAR) studies.,  111  [PMID:26866968] [10.1016/j.ejmech.2016.01.046]

2. Petracca R, Ponzano S, Bertozzi SM, Sasso O, Piomelli D, Bandiera T, Bertozzi F..  (2017)  Progress in the development of β-lactams as N-Acylethanolamine Acid Amidase (NAAA) inhibitors: Synthesis and SAR study of new, potent N-O-substituted derivatives.,  126  [PMID:27915171] [10.1016/j.ejmech.2016.11.039]

3. Tuo W, Leleu-Chavain N, Spencer J, Sansook S, Millet R, Chavatte P..  (2017)  Therapeutic Potential of Fatty Acid Amide Hydrolase, Monoacylglycerol Lipase, and N-Acylethanolamine Acid Amidase Inhibitors.,  60  (1): [PMID:27766867] [10.1021/acs.jmedchem.6b00538]

4. Malamas MS, Farah SI, Lamani M, Pelekoudas DN, Perry NT, Rajarshi G, Miyabe CY, Chandrashekhar H, West J, Pavlopoulos S, Makriyannis A..  (2020)  Design and synthesis of cyanamides as potent and selective N-acylethanolamine acid amidase inhibitors.,  28  (1): [PMID:31761726] [10.1016/j.bmc.2019.115195]

5. Malamas MS, Pavlopoulos S, Alapafuja SO, Farah SI, Zvonok A, Mohammad KA, West J, Perry NT, Pelekoudas DN, Rajarshi G, Shields C, Chandrashekhar H, Wood J, Makriyannis A..  (2021)  Design and Structure-Activity Relationships of Isothiocyanates as Potent and Selective N-Acylethanolamine-Hydrolyzing Acid Amidase Inhibitors.,  64  (9.0): [PMID:33900772] [10.1021/acs.jmedchem.1c00076]

Source

Source(1):

• Scientific Literature