[4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]-carbamic acid benzyl ester

ID: ALA2152090

Chembl Id: CHEMBL2152090

PubChem CID: 71449433

Max Phase: Preclinical

Molecular Formula: C22H25N3O5S

Molecular Weight: 443.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)NC1CCN(S(=O)(=O)c2ccc(NC(=O)OCc3ccccc3)cc2)CC1

Standard InChI:  InChI=1S/C22H25N3O5S/c1-2-21(26)23-19-12-14-25(15-13-19)31(28,29)20-10-8-18(9-11-20)24-22(27)30-16-17-6-4-3-5-7-17/h2-11,19H,1,12-16H2,(H,23,26)(H,24,27)

Standard InChI Key:  WZTJFZPMDNYCQU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2152090

   [4-(4-Acryloylamino-piperidine-1-sulfonyl)-phenyl]carbamic acid benzyl ester

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: 443.53

Molecular Weight (Monoisotopic): 443.1515

AlogP: 2.89

#Rotatable Bonds: 7

Polar Surface Area: 104.81

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: ┄

CX LogP: 2.39

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.64

Np Likeness Score: -1.36

References

1. Prime ME, Brookfield FA, Courtney SM, Gaines S, Marston RW, Ichihara O, Li M, Vaidya D, Williams H, Pedret-Dunn A, Reed L, Schaertl S, Toledo-Sherman L, Beconi M, Macdonald D, Muñoz-Sanjuan I, Dominguez C, Wityak J..  (2012)  Irreversible 4-Aminopiperidine Transglutaminase 2 Inhibitors for Huntington's Disease.,  3  (9): [PMID:24900540] [10.1021/ml3001352]

Source

Source(1):

• Scientific Literature