ID: ALA2337400

Max Phase: Preclinical

Molecular Formula: C22H24N2O6S

Molecular Weight: 444.51

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1c(CCOCCO[N+](=O)[O-])cc(-c2ccc(S(C)(=O)=O)cc2)n1-c1ccccc1

Standard InChI:  InChI=1S/C22H24N2O6S/c1-17-19(12-13-29-14-15-30-24(25)26)16-22(23(17)20-6-4-3-5-7-20)18-8-10-21(11-9-18)31(2,27)28/h3-11,16H,12-15H2,1-2H3

Standard InChI Key:  IIFFGAKIUNZWTM-UHFFFAOYSA-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: 444.51

Molecular Weight (Monoisotopic): 444.1355

AlogP: 3.62

#Rotatable Bonds: 10

Polar Surface Area: 100.67

Molecular Species: NEUTRAL

HBA: 7

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.71

CX LogD: 3.71

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -1.15

References

1. Anzini M, Di Capua A, Valenti S, Brogi S, Rovini M, Giuliani G, Cappelli A, Vomero S, Chiasserini L, Sega A, Poce G, Giorgi G, Calderone V, Martelli A, Testai L, Sautebin L, Rossi A, Pace S, Ghelardini C, Di Cesare Mannelli L, Benetti V, Giordani A, Anzellotti P, Dovizio M, Patrignani P, Biava M..  (2013)  Novel analgesic/anti-inflammatory agents: 1,5-diarylpyrrole nitrooxyalkyl ethers and related compounds as cyclooxygenase-2 inhibiting nitric oxide donors.,  56  (8): [PMID:23534442] [10.1021/jm301370e]

2.  (2013)  1,5-Diaryl-2-alkylpyrrole-3-Substituted Nitro Esters, Selective COX-2 Inhibitors and Nitric Oxide Donors, 

3.  (2015)  1,5-Diary1-2-alkylpyrrole-3-substituted nitro esters, selective COX-2 inhibitors and nitric oxide donors, 

4. Saletti M, Maramai S, Reale A, Paolino M, Brogi S, Di Capua A, Cappelli A, Giorgi G, D'Avino D, Rossi A, Ghelardini C, Di Cesare Mannelli L, Sardella R, Carotti A, Woelkart G, Klösch B, Bigogno C, Dondio G, Anzini M..  (2022)  Novel analgesic/anti-inflammatory agents: 1,5-Diarylpyrrole nitrooxyethyl sulfides and related compounds as Cyclooxygenase-2 inhibitors containing a nitric oxide donor moiety endowed with vasorelaxant properties.,  241  [PMID:35932568] [10.1016/j.ejmech.2022.114615]

Source

Source(3):

• Scientific Literature
• BindingDB Database
• Patent Bioactivity Data