(S)-2-[4-((S)-2-Acetylamino-3-hydroxy-propionylamino)-benzoylamino]-3-methyl-butyric acid

ID: ALA112103

PubChem CID: 10642580

Max Phase: Preclinical

Molecular Formula: C17H23N3O6

Molecular Weight: 365.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N[C@@H](CO)C(=O)Nc1ccc(C(=O)N[C@H](C(=O)O)C(C)C)cc1

Standard InChI:  InChI=1S/C17H23N3O6/c1-9(2)14(17(25)26)20-15(23)11-4-6-12(7-5-11)19-16(24)13(8-21)18-10(3)22/h4-7,9,13-14,21H,8H2,1-3H3,(H,18,22)(H,19,24)(H,20,23)(H,25,26)/t13-,14-/m0/s1

Standard InChI Key:  GJBNZUJANWUXPU-KBPBESRZSA-N

Molfile:  

     RDKit          2D

 26 26  0  0  1  0  0  0  0  0999 V2000
    4.5917   -2.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -3.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9917   -3.3042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -2.4042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0667   -1.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -3.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -3.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -2.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0292   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -4.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  1  1  0
  4  2  1  0
  5  1  1  0
  6  4  1  0
  7  5  1  0
  8 17  1  0
  9  6  1  0
 10  3  1  0
 11  2  2  0
 12  3  2  0
 13  7  2  0
 14  9  2  0
 15 10  2  0
 16 10  1  0
 17 21  1  0
  5 18  1  1
 19  7  1  0
 20 15  1  0
 21 16  2  0
  4 22  1  6
 23 22  1  0
 24  9  1  0
 25 18  1  0
 26 18  1  0
 20 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA112103

   (2S)-2-[[4-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]benzoyl]amino]-3-methylbutanoic 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: 365.39

Molecular Weight (Monoisotopic): 365.1587

AlogP: -0.04

#Rotatable Bonds: 8

Polar Surface Area: 144.83

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.63

CX Basic pKa: ┄

CX LogP: -0.36

CX LogD: -3.70

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -0.58

References

1. Sawa E, Takahashi M, Kamishohara M, Tazunoki T, Kimura K, Arai M, Miyazaki T, Kataoka S, Nishitoba T..  (1999)  Structural modification of Fas C-terminal tripeptide and its effects on the inhibitory activity of Fas/FAP-1 binding.,  42  (17): [PMID:10464015] [10.1021/jm980617f]

2. He, Yantao Y and 11 more authors.  2013-06-27  A potent and selective small-molecule inhibitor for the lymphoid-specific tyrosine phosphatase (LYP), a target associated with autoimmune diseases.  [PMID:23713581]

Source

Source(1):

• Scientific Literature