N-[3-(2-Carbamimidoylsulfanyl-ethoxy)-4-chloro-1-oxo-1H-isochromen-7-yl]-2-phenyl-acetamide

ID: ALA1159882

PubChem CID: 10388060

Max Phase: Preclinical

Molecular Formula: C20H18ClN3O4S

Molecular Weight: 431.90

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)SCCOc1oc(=O)c2cc(NC(=O)Cc3ccccc3)ccc2c1Cl

Standard InChI:  InChI=1S/C20H18ClN3O4S/c21-17-14-7-6-13(24-16(25)10-12-4-2-1-3-5-12)11-15(14)18(26)28-19(17)27-8-9-29-20(22)23/h1-7,11H,8-10H2,(H3,22,23)(H,24,25)

Standard InChI Key:  SCSIOIGBHPIIJR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    3.9250   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9250   -3.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -5.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5000   -3.4167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -3.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -3.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -2.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -3.8125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -2.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000   -5.8792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.6375   -5.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7792   -4.6500    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2042   -4.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -4.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0625   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3500   -4.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0875   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0958   -0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417   -0.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3750    0.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  1  2  0
  5  4  1  0
  6  5  1  0
  7 18  1  0
  8  7  2  0
  9 11  1  0
 10  5  2  0
 11 14  1  0
 12  6  2  0
 13  3  2  0
 14 21  2  0
 15  9  2  0
 16  4  1  0
 17  1  1  0
 18 23  1  0
 19  9  1  0
 20  7  1  0
 21 10  1  0
 22 19  1  0
 23 24  1  0
 24 17  1  0
 25 22  2  0
 26 22  1  0
 27 26  2  0
 28 25  1  0
 29 27  1  0
  3  6  1  0
 14 12  1  0
 28 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1159882

   2-[4-Chloro-1-oxo-7-[(2-phenylacetyl)amino]isochromen-3-yl]oxyethyl carbamimidothioate

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: 431.90

Molecular Weight (Monoisotopic): 431.0707

AlogP: 3.63

#Rotatable Bonds: 7

Polar Surface Area: 118.41

Molecular Species: BASE

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.30

CX Basic pKa: 10.56

CX LogP: 3.51

CX LogD: 1.17

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.30

Np Likeness Score: -1.02

References

1. Kam CM, Kerrigan JE, Plaskon RR, Duffy EJ, Lollar P, Suddath FL, Powers JC..  (1994)  Mechanism-based isocoumarin inhibitors for blood coagulation serine proteases. Effect of the 7-substituent in 7-amino-4-chloro-3-(isothioureidoalkoxy)isocoumarins on inhibitory and anticoagulant potency.,  37  (9): [PMID:8176707] [10.1021/jm00035a009]

Source

Source(1):

• Scientific Literature