(S)-N-(4-carbamimidoylbenzyl)-1-((R)-4-oxo-2-(phenylmethylsulfonamido)-4-(piperazin-1-yl)butanoyl)pyrrolidine-2-carboxamide

ID: ALA1809247

Chembl Id: CHEMBL1809247

PubChem CID: 56683659

Max Phase: Preclinical

Molecular Formula: C28H37N7O5S

Molecular Weight: 583.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(CNC(=O)[C@@H]2CCCN2C(=O)[C@@H](CC(=O)N2CCNCC2)NS(=O)(=O)Cc2ccccc2)cc1

Standard InChI:  InChI=1S/C28H37N7O5S/c29-26(30)22-10-8-20(9-11-22)18-32-27(37)24-7-4-14-35(24)28(38)23(17-25(36)34-15-12-31-13-16-34)33-41(39,40)19-21-5-2-1-3-6-21/h1-3,5-6,8-11,23-24,31,33H,4,7,12-19H2,(H3,29,30)(H,32,37)/t23-,24+/m1/s1

Standard InChI Key:  QZULTDLPYZTNSX-RPWUZVMVSA-N

Alternative Forms

1. Parent:

   

   ALA1809247

   (2S)-1-[(2R)-2-(benzylsulfonylamino)-4-oxo-4-piperazin-1-ylbutanoyl]-N-[(4-carbamimidoylphenyl)methyl]pyrrolidine-2-carboxamide

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: 583.71

Molecular Weight (Monoisotopic): 583.2577

AlogP: -0.11

#Rotatable Bonds: 11

Polar Surface Area: 177.79

Molecular Species: BASE

HBA: 7

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.55

CX Basic pKa: 11.48

CX LogP: -1.41

CX LogD: -3.09

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.18

Np Likeness Score: -1.03

References

1. Sielaff F, Böttcher-Friebertshäuser E, Meyer D, Saupe SM, Volk IM, Garten W, Steinmetzer T..  (2011)  Development of substrate analogue inhibitors for the human airway trypsin-like protease HAT.,  21  (16): [PMID:21741839] [10.1016/j.bmcl.2011.06.033]

Source

Source(1):

• Scientific Literature