4-Carbamoylthiophene-2-carboxylic acid

ID: ALA3617317

Cas Number: 1197877-55-6

PubChem CID: 45792205

Max Phase: Preclinical

Molecular Formula: C6H5NO3S

Molecular Weight: 171.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1csc(C(=O)O)c1

Standard InChI:  InChI=1S/C6H5NO3S/c7-5(8)3-1-4(6(9)10)11-2-3/h1-2H,(H2,7,8)(H,9,10)

Standard InChI Key:  VKHSGKLHGCKCMQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 11  0  0  0  0  0  0  0  0999 V2000
    2.8218   -2.1229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6281   -2.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1385   -3.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394    0.8543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8910    2.0276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5300    0.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  4  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3617317

   4-Carbamoylthiophene-2-carboxylic acid

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: 171.18

Molecular Weight (Monoisotopic): 170.9990

AlogP: 0.55

#Rotatable Bonds: 2

Polar Surface Area: 80.39

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.32

CX Basic pKa: ┄

CX LogP: 0.39

CX LogD: -3.03

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.68

Np Likeness Score: -1.05

References

1. Katane M, Yamada S, Kawaguchi G, Chinen M, Matsumura M, Ando T, Doi I, Nakayama K, Kaneko Y, Matsuda S, Saitoh Y, Miyamoto T, Sekine M, Yamaotsu N, Hirono S, Homma H..  (2015)  Identification of Novel D-Aspartate Oxidase Inhibitors by in Silico Screening and Their Functional and Structural Characterization in Vitro.,  58  (18): [PMID:26322531] [10.1021/acs.jmedchem.5b00871]

2. Raje, Mithun and 9 more authors.  2013-07-01  Synthesis of kojic acid derivatives as secondary binding site probes of D-amino acid oxidase.  [PMID:23683589]

3. Hin, Niyada and 10 more authors.  2015-09-24  6-Hydroxy-1,2,4-triazine-3,5(2H,4H)-dione Derivatives as Novel D-Amino Acid Oxidase Inhibitors.  [PMID:26309148]

4. Hin, Niyada and 8 more authors.  2016-04-15  D-Amino acid oxidase inhibitors based on the 5-hydroxy-1,2,4-triazin-6(1H)-one scaffold.  [PMID:26965861]

5. Kato, Yusuke and 9 more authors.  2018-11-05  Structural basis for potent inhibition of d-amino acid oxidase by thiophene carboxylic acids.  [PMID:30265959]

Source

Source(1):

• Scientific Literature