ID: ALA4218343

Max Phase: Preclinical

Molecular Formula: C22H23N3O5S

Molecular Weight: 441.51

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(COc2ccc(S(=O)(=O)NC3(C(=O)NO)CCC3)cc2)c2ccccc2n1

Standard InChI:  InChI=1S/C22H23N3O5S/c1-15-13-16(19-5-2-3-6-20(19)23-15)14-30-17-7-9-18(10-8-17)31(28,29)25-22(11-4-12-22)21(26)24-27/h2-3,5-10,13,25,27H,4,11-12,14H2,1H3,(H,24,26)

Standard InChI Key:  KFBAFQHSDVTTOZ-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: 441.51

Molecular Weight (Monoisotopic): 441.1358

AlogP: 2.83

#Rotatable Bonds: 7

Polar Surface Area: 117.62

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.68

CX Basic pKa: 5.02

CX LogP: 2.46

CX LogD: 2.44

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.38

Np Likeness Score: -1.08

References

1. Boiteau JG, Ouvry G, Arlabosse JM, Astri S, Beillard A, Bhurruth-Alcor Y, Bonnary L, Bouix-Peter C, Bouquet K, Bourotte M, Cardinaud I, Comino C, Deprez B, Duvert D, Féret A, Hacini-Rachinel F, Harris CS, Luzy AP, Mathieu A, Millois C, Orsini N, Pascau J, Pinto A, Piwnica D, Polge G, Reitz A, Reversé K, Rodeville N, Rossio P, Spiesse D, Tabet S, Taquet N, Tomas L, Vial E, Hennequin LF..  (2018)  Discovery and process development of a novel TACE inhibitor for the topical treatment of psoriasis.,  26  (4): [PMID:28818461] [10.1016/j.bmc.2017.07.054]

Source

Source(1):

• Scientific Literature