2-{3-[4-Chloro-1-oxo-7-(3-phenyl-ureido)-1H-isochromen-3-yloxy]-propyl}-isothiourea

ID: ALA1159883

PubChem CID: 11744313

Max Phase: Preclinical

Molecular Formula: C20H19ClN4O4S

Molecular Weight: 446.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)SCCCOc1oc(=O)c2cc(NC(=O)Nc3ccccc3)ccc2c1Cl

Standard InChI:  InChI=1S/C20H19ClN4O4S/c21-16-14-8-7-13(25-20(27)24-12-5-2-1-3-6-12)11-15(14)17(26)29-18(16)28-9-4-10-30-19(22)23/h1-3,5-8,11H,4,9-10H2,(H3,22,23)(H2,24,25,27)

Standard InChI Key:  ALGXZWBFCBGRKG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.7042   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042   -2.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -1.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -3.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -2.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1292   -1.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -3.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5875   -0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -1.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -1.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -0.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -4.4417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -3.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2750   -3.6292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.7042   -3.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -3.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8417   -3.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5625   -3.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -3.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0333   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0250   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7458   -1.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7500   -1.9625    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 10  1  0
  8 19  1  0
  9  8  2  0
 10 15  1  0
 11  5  2  0
 12  7  1  0
 13  6  2  0
 14  3  2  0
 15 21  2  0
 16  7  2  0
 17  4  1  0
 18  1  1  0
 19 24  1  0
 20  8  1  0
 21 11  1  0
 22 12  1  0
 23 25  1  0
 24 23  1  0
 25 18  1  0
 26 22  2  0
 27 22  1  0
 28 27  2  0
 29 26  1  0
 30 28  1  0
  3  6  1  0
 15 13  1  0
 29 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1159883

   3-[4-Chloro-1-oxo-7-(phenylcarbamoylamino)isochromen-3-yl]oxypropyl 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: 446.92

Molecular Weight (Monoisotopic): 446.0816

AlogP: 4.49

#Rotatable Bonds: 7

Polar Surface Area: 130.44

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.31

CX Basic pKa: 10.50

CX LogP: 3.49

CX LogD: 1.46

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.24

Np Likeness Score: -0.90

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