6-Chloromethyl-2-oxo-2H-chromene-3-carbothioic acid S-phenyl ester

ID: ALA13154

PubChem CID: 44268637

Max Phase: Preclinical

Molecular Formula: C17H11ClO3S

Molecular Weight: 330.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Sc1ccccc1)c1cc2cc(CCl)ccc2oc1=O

Standard InChI:  InChI=1S/C17H11ClO3S/c18-10-11-6-7-15-12(8-11)9-14(16(19)21-15)17(20)22-13-4-2-1-3-5-13/h1-9H,10H2

Standard InChI Key:  WIBPRJHSRYQIFR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    7.2417   -2.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2417   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4750   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0042   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4792   -3.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7667   -2.5792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.0125   -3.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0000   -1.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5292   -2.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1875   -3.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -1.2792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3000   -2.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5250   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2875   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0625   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0542   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  1  1  0
  5  2  1  0
  6  3  1  0
  7  6  1  0
  8  4  1  0
  9  2  2  0
 10  4  2  0
 11  6  2  0
 12  7  2  0
 13  8  1  0
 14 11  1  0
 15 14  2  0
 16 17  1  0
 17 14  1  0
 18 13  2  0
 19 13  1  0
 20 19  2  0
 21 18  1  0
 22 20  1  0
  7  5  1  0
 15 12  1  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA13154

   S-phenyl 6-(chloromethyl)-2-oxochromene-3-carbothioate

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: 330.79

Molecular Weight (Monoisotopic): 330.0117

AlogP: 4.46

#Rotatable Bonds: 3

Polar Surface Area: 47.28

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.40

Np Likeness Score: -0.69

References

1. Wouters J, Huygens M, Pochet L, Pirotte B, Durant F, Masereel B..  (2002)  Structural approach of the mechanism of inhibition of alpha-chymotrypsin by coumarins.,  12  (7): [PMID:11909728] [10.1016/s0960-894x(02)00073-2]

Source

Source(1):

• Scientific Literature