(S)-2-(2-(benzo[d][1,3]dioxol-5-yl)-4-oxo-4,5-dihydrothiazol-5-yl)acetic acid

ID: ALA4533016

PubChem CID: 6930335

Max Phase: Preclinical

Molecular Formula: C12H9NO5S

Molecular Weight: 279.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@@H]1SC(c2ccc3c(c2)OCO3)=NC1=O

Standard InChI:  InChI=1S/C12H9NO5S/c14-10(15)4-9-11(16)13-12(19-9)6-1-2-7-8(3-6)18-5-17-7/h1-3,9H,4-5H2,(H,14,15)/t9-/m0/s1

Standard InChI Key:  VAIURZVRAALGEN-VIFPVBQESA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   32.0052   -9.9631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0041  -10.7826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7121  -11.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7104   -9.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4190   -9.9595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4238  -10.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2038  -11.0266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6812  -10.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1960   -9.7020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2988  -11.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5525  -10.8610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0052  -11.4679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4133  -12.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2127  -12.0065    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   29.1925  -11.3818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.0803  -12.9222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2676  -13.0071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9347  -13.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7877  -12.3456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  2 10  1  0
 12 15  2  0
 13 16  1  1
 16 17  1  0
 17 18  1  0
 17 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533016

   2-[(5S)-2-(1,3-benzodioxol-5-yl)-4-oxo-1,3-thiazol-5-yl]acetic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 279.27

Molecular Weight (Monoisotopic): 279.0201

AlogP: 1.28

#Rotatable Bonds: 3

Polar Surface Area: 85.19

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.22

CX Basic pKa: ┄

CX LogP: 1.02

CX LogD: -2.74

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.90

Np Likeness Score: -0.20

References

1. Ruiz V, Czyzyk DJ, Valhondo M, Jorgensen WL, Anderson KS..  (2019)  Novel allosteric covalent inhibitors of bifunctional Cryptosporidium hominis TS-DHFR from parasitic protozoa identified by virtual screening.,  29  (11): [PMID:30929953] [10.1016/j.bmcl.2019.03.022]

Source

Source(1):

• Scientific Literature