ID: ALA2419820

Max Phase: Preclinical

Molecular Formula: C13H15NO4

Molecular Weight: 249.27

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@H]1OC(=O)[C@@H]1NC(=O)OCCc1ccccc1

Standard InChI:  InChI=1S/C13H15NO4/c1-9-11(12(15)18-9)14-13(16)17-8-7-10-5-3-2-4-6-10/h2-6,9,11H,7-8H2,1H3,(H,14,16)/t9-,11+/m0/s1

Standard InChI Key:  VIOAYNDATRYIHB-GXSJLCMTSA-N

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

Properties

Molecular Weight: 249.27

Molecular Weight (Monoisotopic): 249.1001

AlogP: 1.27

#Rotatable Bonds: 4

Polar Surface Area: 64.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.11

CX Basic pKa:

CX LogP: 1.91

CX LogD: 1.91

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.82

Np Likeness Score: 0.48

References

1. Ponzano S, Bertozzi F, Mengatto L, Dionisi M, Armirotti A, Romeo E, Berteotti A, Fiorelli C, Tarozzo G, Reggiani A, Duranti A, Tarzia G, Mor M, Cavalli A, Piomelli D, Bandiera T..  (2013)  Synthesis and structure-activity relationship (SAR) of 2-methyl-4-oxo-3-oxetanylcarbamic acid esters, a class of potent N-acylethanolamine acid amidase (NAAA) inhibitors.,  56  (17): [PMID:23991897] [10.1021/jm400739u]

2. Ponzano S, Berteotti A, Petracca R, Vitale R, Mengatto L, Bandiera T, Cavalli A, Piomelli D, Bertozzi F, Bottegoni G..  (2014)  Synthesis, biological evaluation, and 3D QSAR study of 2-methyl-4-oxo-3-oxetanylcarbamic acid esters as N-acylethanolamine acid amidase (NAAA) inhibitors.,  57  (23): [PMID:25380517] [10.1021/jm501455s]

3.  (2016)  Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA), 

Source

Source(2):

• Scientific Literature
• BindingDB Database