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

ID: ALA323167

PubChem CID: 10498671

Max Phase: Preclinical

Molecular Formula: C16H29N3O6

Molecular Weight: 359.42

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C16H29N3O6/c1-8(2)6-11(14(22)19-13(9(3)4)16(24)25)18-15(23)12(7-20)17-10(5)21/h8-9,11-13,20H,6-7H2,1-5H3,(H,17,21)(H,18,23)(H,19,22)(H,24,25)/t11-,12+,13+/m1/s1

Standard InChI Key:  ORIIRLCDJGETQD-AGIUHOORSA-N

Molfile:  

     RDKit          2D

 25 24  0  0  1  0  0  0  0  0999 V2000
    1.8125   -3.9667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -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
   -0.7875   -3.6667    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
    0.7667   -3.9667    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
    2.8500   -4.5667    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
   -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
   -0.2708   -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
    2.8500   -2.7667    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
   -0.1333   -5.0667    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
  2  4  1  0
  3  1  1  0
  4  7  1  0
  5  2  1  0
  6  1  1  0
  7  3  1  0
  8  5  1  0
  9  6  1  0
 10  8  1  0
 11  2  2  0
 12  3  2  0
 13  9  2  0
  7 14  1  1
 15 10  2  0
  6 16  1  1
 17  9  1  0
  5 18  1  1
 19 18  1  0
 20 14  1  0
 21 10  1  0
 22 16  1  0
 23 16  1  0
 24 20  1  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA323167

   Ac-Ser-D-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: 359.42

Molecular Weight (Monoisotopic): 359.2056

AlogP: -0.76

#Rotatable Bonds: 10

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: 3.97

CX Basic pKa: ┄

CX LogP: -0.74

CX LogD: -3.91

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.35

Np Likeness Score: 0.27

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