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

ID: ALA113027

PubChem CID: 10853969

Max Phase: Preclinical

Molecular Formula: C14H25N3O6

Molecular Weight: 331.37

Molecule Type: Protein

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H25N3O6/c1-7(2)10(12(21)22)16-13(23)14(4,5)17-11(20)9(6-18)15-8(3)19/h7,9-10,18H,6H2,1-5H3,(H,15,19)(H,16,23)(H,17,20)(H,21,22)/t9-,10-/m0/s1

Standard InChI Key:  CWOSGTNZAAQWPL-UWVGGRQHSA-N

Molfile:  

     RDKit          2D

 23 22  0  0  1  0  0  0  0  0999 V2000
    3.5542   -3.0042    0.0000 N   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
    1.4750   -3.0042    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
    0.9542   -3.3042    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
    4.0667   -3.3042    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
    4.5917   -3.0042    0.0000 C   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
    3.0292   -3.9042    0.0000 O   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
    4.5917   -2.4042    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
    4.0667   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -3.3042    0.0000 O   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
    2.0875   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9292   -2.5792    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
    4.5917   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -4.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  6  1  0
  5  3  1  0
  6  2  1  0
  7  1  1  0
  8  5  1  0
  9  7  1  0
 10  8  1  0
 11  2  2  0
 12  3  2  0
 13  9  2  0
 14 10  2  0
  7 15  1  6
 16  9  1  0
  5 17  1  6
 18  6  1  0
 19  6  1  0
 20 17  1  0
 21 10  1  0
 22 15  1  0
 23 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA113027

   Ac-Ser-Aib-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: 331.37

Molecular Weight (Monoisotopic): 331.1743

AlogP: -1.40

#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: 3.87

CX Basic pKa: ┄

CX LogP: -1.56

CX LogD: -4.79

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.37

Np Likeness Score: -0.13

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