2-[2-(4-Carbamimidoyl-benzenesulfonylamino)-acetylamino]-3-(4-carbamimidoyl-phenyl)-propionic acid

ID: ALA341933

PubChem CID: 10095093

Max Phase: Preclinical

Molecular Formula: C19H22N6O5S

Molecular Weight: 446.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)c1ccc(CC(NC(=O)CNS(=O)(=O)c2ccc(C(=N)N)cc2)C(=O)O)cc1

Standard InChI:  InChI=1S/C19H22N6O5S/c20-17(21)12-3-1-11(2-4-12)9-15(19(27)28)25-16(26)10-24-31(29,30)14-7-5-13(6-8-14)18(22)23/h1-8,15,24H,9-10H2,(H3,20,21)(H3,22,23)(H,25,26)(H,27,28)

Standard InChI Key:  MREBMJAXNFLJHN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
    6.7167   -0.6875    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -0.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6375    2.4708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042    1.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042    0.5583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7000   -0.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -1.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -0.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750    2.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542    3.0708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0375   -2.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875    0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667    1.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -0.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1542   -1.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542    2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3250   -2.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1000    2.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    1.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875    1.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    1.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917    1.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  7  1  0
  4 14  1  0
  5 13  1  0
  6  3  1  0
  7  9  1  0
  8  1  1  0
  9 10  1  0
 10  2  1  0
 11  1  2  0
 12  1  2  0
 13 22  1  0
 14 25  2  0
 15  4  2  0
 16  5  2  0
 17  3  1  0
 18  6  2  0
 19  9  2  0
 20  8  2  0
 21  8  1  0
 22 21  2  0
 23 20  1  0
 24 30  2  0
 25 31  1  0
 26  5  1  0
 27  4  1  0
 28 17  1  0
 29  6  1  0
 30 28  1  0
 31 28  2  0
 13 23  2  0
 14 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA341933

   2-[2-(4-Carbamimidoyl-benzenesulfonylamino)-acetylamino]-3-(4-carbamimidoyl-phenyl)-propionic acid

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: 446.49

Molecular Weight (Monoisotopic): 446.1372

AlogP: -0.65

#Rotatable Bonds: 10

Polar Surface Area: 212.31

Molecular Species: ZWITTERION

HBA: 6

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.12

CX Basic pKa: 11.60

CX LogP: -3.45

CX LogD: -4.73

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.18

Np Likeness Score: -0.62

References

1. Gabriel B, Stubbs MT, Bergner A, Hauptmann J, Bode W, Stürzebecher J, Moroder L..  (1998)  Design of benzamidine-type inhibitors of factor Xa.,  41  (22): [PMID:9784099] [10.1021/jm980227t]

Source

Source(1):

• Scientific Literature