(S)-2-{(S)-2-[((S)-2-Acetylamino-3-hydroxy-propionyl)-methyl-amino]-4-methyl-pentanoylamino}-3-methyl-butyric acid

ID: ALA324280

PubChem CID: 11793731

Max Phase: Preclinical

Molecular Formula: C17H31N3O6

Molecular Weight: 373.45

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H31N3O6/c1-9(2)7-13(15(23)19-14(10(3)4)17(25)26)20(6)16(24)12(8-21)18-11(5)22/h9-10,12-14,21H,7-8H2,1-6H3,(H,18,22)(H,19,23)(H,25,26)/t12-,13-,14-/m0/s1

Standard InChI Key:  HQHOIMBUUFXJNE-IHRRRGAJSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  1  0  0  0  0  0999 V2000
   -0.2708   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -3.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -3.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083   -3.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -3.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7667   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -4.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -3.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -3.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2542   -3.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -2.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -5.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  1  0
  4  2  1  0
  5  1  1  0
  6  3  1  0
  7  4  1  0
  8  5  1  0
  9  7  1  0
 10  8  1  0
 11  1  2  0
 12  2  2  0
  6 13  1  6
 14  9  2  0
 15 10  2  0
  7 16  1  1
 17  9  1  0
  5 18  1  1
 19  3  1  0
 20 18  1  0
 21 13  1  0
 22 10  1  0
 23 16  1  0
 24 16  1  0
 25 21  1  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA324280

   Ac-Ser-N(Me)Leu-Val-OH

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Protein

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 373.45

Molecular Weight (Monoisotopic): 373.2213

AlogP: -0.42

#Rotatable Bonds: 10

Polar Surface Area: 136.04

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.02

CX Basic pKa: ┄

CX LogP: -0.51

CX LogD: -3.66

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.41

Np Likeness Score: 0.32

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