4-(2-(1-((4-carbamoylphenoxy)methyl)cyclopentylamino)acetyl)-3H-thiophenium

ID: ALA541664

PubChem CID: 16725905

Max Phase: Preclinical

Molecular Formula: C19H22N2O3S

Molecular Weight: 358.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1ccc(OCC2(NCC(=O)c3ccsc3)CCCC2)cc1

Standard InChI:  InChI=1S/C19H22N2O3S/c20-18(23)14-3-5-16(6-4-14)24-13-19(8-1-2-9-19)21-11-17(22)15-7-10-25-12-15/h3-7,10,12,21H,1-2,8-9,11,13H2,(H2,20,23)

Standard InChI Key:  LMKXIVHWGZZOBT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    8.4667   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7792   -6.7542    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.2250   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5542   -7.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3250   -6.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6125   -6.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3667   -7.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -4.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -6.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -5.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -4.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6042   -5.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -6.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8917   -6.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -5.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -6.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0250   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -6.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -7.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  1  0
  4  5  1  0
  5  1  2  0
  6 14  1  0
  7  1  1  0
  8 12  1  0
  9  8  1  0
 10  7  2  0
 11  2  2  0
 12  3  1  0
 13  3  2  0
 14 20  2  0
 15 21  1  0
 16  2  1  0
 17 18  1  0
 18  9  1  0
 19 17  1  0
 20 19  1  0
 21 19  2  0
 22  9  1  0
 23  9  1  0
 24 23  1  0
 25 22  1  0
  4 10  1  0
 24 25  1  0
 15  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA541664

   4-[(1-{[2-Oxo-2-(thiophen-3-yl)ethyl]amino}cyclopentyl)methoxy]benzamide

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: 358.46

Molecular Weight (Monoisotopic): 358.1351

AlogP: 3.01

#Rotatable Bonds: 8

Polar Surface Area: 81.42

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.71

CX LogP: 2.59

CX LogD: 2.11

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -0.75

References

1. Sheehan SM, Mest HJ, Watson BM, Klimkowski VJ, Timm DE, Cauvin A, Parsons SH, Shi Q, Canada EJ, Wiley MR, Ruehter G, Evers B, Petersen S, Blaszczak LC, Pulley SR, Margolis BJ, Wishart GN, Renson B, Hankotius D, Mohr M, Zechel JC, Michael Kalbfleisch J, Dingess-Hammond EA, Boelke A, Weichert AG..  (2007)  Discovery of non-covalent dipeptidyl peptidase IV inhibitors which induce a conformational change in the active site.,  17  (6): [PMID:17239592] [10.1016/j.bmcl.2006.12.074]

Source

Source(1):

• Scientific Literature