(S)-(4)-(ethylsulfonyl)benzoylalanine

ID: ALA3629572

PubChem CID: 11652132

Max Phase: Preclinical

Molecular Formula: C12H15NO5S

Molecular Weight: 285.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)c1ccc(C(=O)C[C@H](N)C(=O)O)cc1

Standard InChI:  InChI=1S/C12H15NO5S/c1-2-19(17,18)9-5-3-8(4-6-9)11(14)7-10(13)12(15)16/h3-6,10H,2,7,13H2,1H3,(H,15,16)/t10-/m0/s1

Standard InChI Key:  JLNPBBSGBIACRH-JTQLQIEISA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    2.5984    2.7004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5988    1.5004    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6377    2.1009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9336   -3.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8509   -5.8560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9292   -5.8600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    0.7508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9382    1.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  1
 14 16  1  0
 14 17  2  0
  5  2  1  0
  2 18  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3629572

   (2S)-2-amino-4-(4-ethylsulfonylphenyl)-4-oxobutanoic 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: 285.32

Molecular Weight (Monoisotopic): 285.0671

AlogP: 0.46

#Rotatable Bonds: 6

Polar Surface Area: 114.53

Molecular Species: ZWITTERION

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.90

CX Basic pKa: 8.56

CX LogP: -2.38

CX LogD: -2.41

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.73

Np Likeness Score: -0.64

References

1. Dounay AB, Tuttle JB, Verhoest PR..  (2015)  Challenges and Opportunities in the Discovery of New Therapeutics Targeting the Kynurenine Pathway.,  58  (22): [PMID:26207924] [10.1021/acs.jmedchem.5b00461]

2. Pellicciari R, Liscio P, Giacchè N, De Franco F, Carotti A, Robertson J, Cialabrini L, Katsyuba E, Raffaelli N, Auwerx J..  (2018)  α-Amino-β-carboxymuconate-ε-semialdehyde Decarboxylase (ACMSD) Inhibitors as Novel Modulators of De Novo Nicotinamide Adenine Dinucleotide (NAD+) Biosynthesis.,  61  (3): [PMID:29345930] [10.1021/acs.jmedchem.7b01254]

Source

Source(1):

• Scientific Literature