1-{[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]amino}cyclobutanecarboxylic acid

ID: ALA228170

PubChem CID: 9930716

Max Phase: Preclinical

Molecular Formula: C15H16ClN5O4S

Molecular Weight: 397.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(N)=Nc1ncc(Cl)c2ccc(S(=O)(=O)NC3(C(=O)O)CCC3)cc12

Standard InChI:  InChI=1S/C15H16ClN5O4S/c16-11-7-19-12(20-14(17)18)10-6-8(2-3-9(10)11)26(24,25)21-15(13(22)23)4-1-5-15/h2-3,6-7,21H,1,4-5H2,(H,22,23)(H4,17,18,19,20)

Standard InChI Key:  DEPFCMSTRPLWNG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    4.1568   -5.5112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7396   -4.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1526   -4.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5697   -4.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3039   -4.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3027   -5.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0171   -5.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0153   -3.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7301   -4.2856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7309   -5.1119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4457   -5.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1602   -5.1081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1555   -4.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4401   -3.8718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4474   -6.3470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1623   -6.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1640   -7.5821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.8754   -6.3441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884   -5.5278    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688   -5.9340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9969   -6.2439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1816   -4.8106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4409   -5.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7309   -5.5012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4330   -6.7446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4358   -3.0468    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
  6  7  1  0
 13 14  2  0
 14  9  1  0
  7 10  2  0
 11 15  1  0
  3  4  1  0
 15 16  2  0
  9  8  2  0
 16 17  1  0
  8  5  1  0
 16 18  1  0
  4  1  1  0
  6 19  1  0
 19 20  1  0
  9 10  1  0
 19 21  2  0
  1  2  1  0
 19 22  2  0
 10 11  1  0
 20  1  1  0
  5  6  2  0
  1 23  1  0
 11 12  2  0
 23 24  1  0
  2  3  1  0
 23 25  2  0
 14 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA228170

   Substituted glycine deriv. 27

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: 397.84

Molecular Weight (Monoisotopic): 397.0612

AlogP: 1.08

#Rotatable Bonds: 5

Polar Surface Area: 160.76

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.58

CX Basic pKa: 8.01

CX LogP: 0.21

CX LogD: 0.12

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.43

Np Likeness Score: -0.84

References

1. Fish PV, Barber CG, Brown DG, Butt R, Collis MG, Dickinson RP, Henry BT, Horne VA, Huggins JP, King E, O'Gara M, McCleverty D, McIntosh F, Phillips C, Webster R..  (2007)  Selective urokinase-type plasminogen activator inhibitors. 4. 1-(7-sulfonamidoisoquinolinyl)guanidines.,  50  (10): [PMID:17447747] [10.1021/jm061066t]

Source

Source(1):

• Scientific Literature