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

ID: ALA109876

PubChem CID: 44340708

Max Phase: Preclinical

Molecular Formula: C17H31N3O6

Molecular Weight: 373.45

Molecule Type: Protein

Names and Identifiers

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

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

Standard InChI Key:  BRIGIKGUSAHAGE-IHRRRGAJSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  1  0  0  0  0  0999 V2000
    7.1542   -4.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125   -3.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8667   -4.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5875   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -3.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -5.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4417   -3.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5875   -5.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -5.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -3.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8667   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3000   -3.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -2.6917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -5.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -4.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1542   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3000   -3.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -5.8875    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  6
 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 17  1  0
 25 20  1  0
 26 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA109876

   Ac-Ser-Leu-Val-OMe

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: -0.67

#Rotatable Bonds: 10

Polar Surface Area: 133.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.87

CX Basic pKa: ┄

CX LogP: -0.59

CX LogD: -0.59

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: 0.22

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