(S)-2-[(S)-2-((S)-2-Acetylamino-3-hydroxy-propionylamino)-4-methyl-pentanoylamino]-3-methyl-butyric acid 2H-tetrazol-5-yl ester

ID: ALA442200

PubChem CID: 44340416

Max Phase: Preclinical

Molecular Formula: C17H29N7O6

Molecular Weight: 427.46

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)Oc1nn[nH]n1)C(C)C

Standard InChI:  InChI=1S/C17H29N7O6/c1-8(2)6-11(19-15(28)12(7-25)18-10(5)26)14(27)20-13(9(3)4)16(29)30-17-21-23-24-22-17/h8-9,11-13,25H,6-7H2,1-5H3,(H,18,26)(H,19,28)(H,20,27)(H,21,22,23,24)/t11-,12-,13-/m0/s1

Standard InChI Key:  FKDBIITUDNKYRY-AVGNSLFASA-N

Molfile:  

     RDKit          2D

 30 30  0  0  1  0  0  0  0  0999 V2000
    6.6500   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2000   -3.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7125   -4.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7375   -3.5917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1292   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4125   -4.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -3.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -3.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500   -3.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -3.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -4.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -4.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292   -4.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0875   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -2.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -2.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -5.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  2  0
  5  6  1  0
  6  1  1  0
  7  3  1  0
  8 13  1  0
  9 11  1  0
 10  8  1  0
 11 14  1  0
 12  9  1  0
 13  5  1  0
 14 10  1  0
 15 12  1  0
 16 15  1  0
 17  5  2  0
 18  9  2  0
 19 10  2  0
 14 20  1  6
 21 16  2  0
 13 22  1  1
 12 23  1  1
 24 23  1  0
 25 20  1  0
 26 16  1  0
 27 22  1  0
 28 22  1  0
 29 25  1  0
 30 25  1  0
  4  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA442200

   2H-tetrazol-5-yl (2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoate

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: 427.46

Molecular Weight (Monoisotopic): 427.2179

AlogP: -1.73

#Rotatable Bonds: 11

Polar Surface Area: 188.29

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.05

CX Basic pKa: ┄

CX LogP: -0.60

CX LogD: -2.14

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: -0.28

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