4-(2-aminophenyl)-4-oxo-2-methylthiobutanoic acid

ID: ALA448235

PubChem CID: 9991835

Max Phase: Preclinical

Molecular Formula: C11H13NO3S

Molecular Weight: 239.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: thiobutacin | thiobutacin|CHEMBL448235|SCHEMBL5901097|4-(2-aminophenyl)-2-methylsulfanyl-4-oxobutanoic acid

Canonical SMILES:  CSC(CC(=O)c1ccccc1N)C(=O)O

Standard InChI:  InChI=1S/C11H13NO3S/c1-16-10(11(14)15)6-9(13)7-4-2-3-5-8(7)12/h2-5,10H,6,12H2,1H3,(H,14,15)

Standard InChI Key:  DGBICJRAEAUCGO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -5.1850    0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1863   -0.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4734   -0.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7541   -0.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7573    0.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4753    0.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0393   -0.7347    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0449    0.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3284    0.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0489    1.7491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6160    0.9313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.5224    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1872    0.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6196    1.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9072    2.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3361    2.1679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  8  1  0
  8  9  1  0
  4  5  1  0
  8 10  2  0
  2  3  1  0
  9 11  1  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
  4  7  1  0
  3  4  2  0
 14 15  1  0
 14 16  2  0
 11 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA448235

   THIOBUTACIN

Molecule Features

Natural Product: Yes

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: 239.30

Molecular Weight (Monoisotopic): 239.0616

AlogP: 1.66

#Rotatable Bonds: 5

Polar Surface Area: 80.39

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.10

CX Basic pKa: 2.40

CX LogP: 1.72

CX LogD: -1.24

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.60

Np Likeness Score: 0.26

References

1. Lee JY, Moon SS, Yun BS, Yoo ID, Hwang BK..  (2004)  Thiobutacin, a novel antifungal and antioomycete antibiotic from Lechevalieria aerocolonigenes.,  67  (12): [PMID:15620255] [10.1021/np049786v]

Source

Source(1):

• Scientific Literature