N-[(4-chloro-1-guanidino-7-isoquinolinyl)sulphonyl]-D-proline

ID: ALA227990

PubChem CID: 9843775

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)N3CCC[C@@H]3C(=O)O)cc12

Standard InChI:  InChI=1S/C15H16ClN5O4S/c16-11-7-19-13(20-15(17)18)10-6-8(3-4-9(10)11)26(24,25)21-5-1-2-12(21)14(22)23/h3-4,6-7,12H,1-2,5H2,(H,22,23)(H4,17,18,19,20)/t12-/m1/s1

Standard InChI Key:  MWEYSFQTTAFUFL-GFCCVEGCSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
  -23.8440   93.0300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -23.1296   93.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -22.4151   93.0300    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -22.4151   92.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -23.1296   91.7925    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -23.1296   90.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -22.4151   90.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -22.4151   89.7300    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  -21.7006   90.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -20.9861   90.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -20.2717   90.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -20.2717   91.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -20.9861   92.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -21.7006   91.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.5572   92.2050    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -19.1447   91.4905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -19.9697   92.9195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8427   92.6175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -18.0891   92.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.5370   92.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.9495   93.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -18.7565   93.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -19.3696   93.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -20.1542   93.7351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -19.1981   94.7970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -23.1296   94.2675    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  2  0
  2 26  1  0
  4  3  1  0
  4  5  1  0
 14  4  2  0
  6  5  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
 10  9  1  0
 14  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 15  1  0
 13 14  1  0
 16 15  2  0
 17 15  2  0
 18 15  1  0
 19 18  1  0
 22 18  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 23 24  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA227990

   1-({4-Chloro-1-[(Diaminomethylidene)amino]isoquinolin-7-Yl}sulfonyl)-D-Proline

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: 1.03

#Rotatable Bonds: 4

Polar Surface Area: 151.97

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.63

CX Basic pKa: 8.03

CX LogP: -0.08

CX LogD: -0.17

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.19

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