3,5-Dichloro-4-((S)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(((S)-1-((3-(dimethylcarbamoyl)-phenyl)sulfonyl)pyrrolidine-2-carbonyl)oxy)ethyl)pyridine1-Oxide

ID: ALA4093768

Chembl Id: CHEMBL4093768

PubChem CID: 71092519

Max Phase: Preclinical

Molecular Formula: C32H33Cl2F2N3O8S

Molecular Weight: 728.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)C(=O)c1cccc(S(=O)(=O)N2CCC[C@H]2C(=O)O[C@@H](Cc2c(Cl)c[n+]([O-])cc2Cl)c2ccc(OC(F)F)c(OCC3CC3)c2)c1

Standard InChI:  InChI=1S/C32H33Cl2F2N3O8S/c1-37(2)30(40)21-5-3-6-22(13-21)48(43,44)39-12-4-7-26(39)31(41)46-28(15-23-24(33)16-38(42)17-25(23)34)20-10-11-27(47-32(35)36)29(14-20)45-18-19-8-9-19/h3,5-6,10-11,13-14,16-17,19,26,28,32H,4,7-9,12,15,18H2,1-2H3/t26-,28-/m0/s1

Standard InChI Key:  MTVYRGXACZGKJC-XCZPVHLTSA-N

Alternative Forms

1. Parent:

   

   ALA4093768

   [(1S)-1-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-2-(3,5-dichloro-1-oxidopyridin-1-ium-4-yl)ethyl] (2S)-1-[3-(dimethylcarbamoyl)phenyl]sulfonylpyrrolidine-2-carboxylate

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: 728.60

Molecular Weight (Monoisotopic): 727.1333

AlogP: 5.40

#Rotatable Bonds: 13

Polar Surface Area: 129.39

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 0.13

CX LogP: 4.49

CX LogD: 4.49

Aromatic Rings: 3

Heavy Atoms: 48

QED Weighted: 0.13

Np Likeness Score: -1.34

References

1. Carzaniga L, Amari G, Rizzi A, Capaldi C, De Fanti R, Ghidini E, Villetti G, Carnini C, Moretto N, Facchinetti F, Caruso P, Marchini G, Battipaglia L, Patacchini R, Cenacchi V, Volta R, Amadei F, Pappani A, Capacchi S, Bagnacani V, Delcanale M, Puccini P, Catinella S, Civelli M, Armani E..  (2017)  Discovery and Optimization of Thiazolidinyl and Pyrrolidinyl Derivatives as Inhaled PDE4 Inhibitors for Respiratory Diseases.,  60  (24): [PMID:29200281] [10.1021/acs.jmedchem.7b01044]

Source

Source(1):

• Scientific Literature