2-(4-Phenoxybutanamido)thiazole-5-carboxylic acid

ID: ALA4538493

PubChem CID: 155549469

Max Phase: Preclinical

Molecular Formula: C14H14N2O4S

Molecular Weight: 306.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCCOc1ccccc1)Nc1ncc(C(=O)O)s1

Standard InChI:  InChI=1S/C14H14N2O4S/c17-12(16-14-15-9-11(21-14)13(18)19)7-4-8-20-10-5-2-1-3-6-10/h1-3,5-6,9H,4,7-8H2,(H,18,19)(H,15,16,17)

Standard InChI Key:  KPEFYSJGGSTAON-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   40.7137   -4.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.7125   -5.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4206   -5.9665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1303   -5.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.1274   -4.7344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.4188   -4.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.0059   -4.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2983   -4.7384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5905   -4.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8829   -4.7387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1751   -4.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4674   -4.7390    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.1749   -3.5131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7596   -4.3306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6729   -3.5195    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.8735   -3.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4651   -4.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0121   -4.6647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5410   -2.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0212   -1.9421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.7282   -2.5181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  1  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  2  0
 16 19  1  0
 19 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4538493

   ---

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: 306.34

Molecular Weight (Monoisotopic): 306.0674

AlogP: 2.64

#Rotatable Bonds: 7

Polar Surface Area: 88.52

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.21

CX Basic pKa: ┄

CX LogP: 2.39

CX LogD: -1.13

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: -1.60

References

1. Nguyen W, Jacobson J, Jarman KE, Jousset Sabroux H, Harty L, McMahon J, Lewin SR, Purcell DF, Sleebs BE..  (2019)  Identification of 5-Substituted 2-Acylaminothiazoles That Activate Tat-Mediated Transcription in HIV-1 Latency Models.,  62  (10): [PMID:30973727] [10.1021/acs.jmedchem.9b00462]

Source

Source(1):

• Scientific Literature